GB782062A - Improvements relating to quinoline compounds - Google Patents
Improvements relating to quinoline compoundsInfo
- Publication number
- GB782062A GB782062A GB24953/55A GB2495355A GB782062A GB 782062 A GB782062 A GB 782062A GB 24953/55 A GB24953/55 A GB 24953/55A GB 2495355 A GB2495355 A GB 2495355A GB 782062 A GB782062 A GB 782062A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonic acid
- quinoline
- hydroxybenzo
- hydroxy
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- HCRQCJYXFYXROL-UHFFFAOYSA-N N-(8-hydroxynaphthalen-1-yl)-3-oxobutanamide Chemical compound OC1=CC=CC2=CC=CC(=C12)NC(CC(=O)C)=O HCRQCJYXFYXROL-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- ABLZMHBYCVGCPV-UHFFFAOYSA-N 1-(2-amino-8-hydroxynaphthalen-1-yl)butane-1,3-dione Chemical compound C(CC(=O)C)(=O)C1=C(C=CC2=CC=CC(=C12)O)N ABLZMHBYCVGCPV-UHFFFAOYSA-N 0.000 abstract 1
- NNWYOMXEYRMKEU-UHFFFAOYSA-N N-(1-hydroxynaphthalen-2-yl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1=C(C2=CC=CC=C2C=C1)O NNWYOMXEYRMKEU-UHFFFAOYSA-N 0.000 abstract 1
- GSIRQXKKXVCPAG-UHFFFAOYSA-N N-(5-hydroxynaphthalen-2-yl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1=CC2=CC=CC(=C2C=C1)O GSIRQXKKXVCPAG-UHFFFAOYSA-N 0.000 abstract 1
- CHLQTSOPMNBKGD-UHFFFAOYSA-N N-(6-hydroxynaphthalen-2-yl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1=CC2=CC=C(C=C2C=C1)O CHLQTSOPMNBKGD-UHFFFAOYSA-N 0.000 abstract 1
- ZFPJHJXGJWUCQN-UHFFFAOYSA-N N-(8-hydroxynaphthalen-2-yl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC=1C=CC2=CC=CC(=C2C1)O ZFPJHJXGJWUCQN-UHFFFAOYSA-N 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- -1 aluminium chloride-sodium chloride Chemical compound 0.000 abstract 1
- VNICJHGMMYPVLC-UHFFFAOYSA-K aluminum;n,n-diethylethanamine;trichloride Chemical compound [Al+3].[Cl-].[Cl-].[Cl-].CCN(CC)CC VNICJHGMMYPVLC-UHFFFAOYSA-K 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 2-hydroxy-4-methyl-5: 6- or -7: 8-(hydroxybenzo)-quinoline sulphonic acids of the formula <FORM:0782062/IV (a)/1> or <FORM:0782062/IV (a)/2> where n is 1 or 2. The compounds are prepared by treating an acetoacetylaminonaphthol sulphonic acid having a free ortho-position to the acetoacetylated amino group and containing at most two SO3H groups with a strong mineral acid or in an aluminium chloride melt as a dehydrating, ring closing agent. Specified dehydrating, ring closing agents are concentrated phosphoric, hydrochloric and sulphuric acids, with or without the addition of aluminium chloride; aluminium chloride-sodium chloride and aluminium chloride-triethylamine melts. Specified starting materials are 2-acetoacetylamino - 5 - naphthol - 7 - sulphonic acid, 2 - acetoacetylamino - 8 - naphthol - 6 - sulphonic acid, 2 - acetoacetylamino - 6 - naphthol - 8 - sulphonic acid, 1 - acetoacetylamino - 5 - naphthol-7-sulphonic acid, 1-acetoacetylamino-8-naphthol - 5 - sulphonic acid, 1 - acetoacetyl-amino - 8 - naphthol - 6 - sulphonic acid, 1 - acetoacetylamino - 8 - naphthol - 3 : 6 - sulphonic acid and 1-acetoacetylamino-4 : 6-disulphonic acid. The examples describe the preparation of sodium salts of 2-hydroxy-4-methyl-5 : 6-(31-hydroxybenzo) - quinoline - 51 - sulphonic acid, 2 - hydroxy - 4 - methyl - 5 : 6 - (61 - hydroxybenzo) - quinoline - 41 - sulphonic acid, 2-hydroxy - 4 - methyl - 5 : 6 - (41 - hydroxybenzo) - quinoline - 61 - sulphonic acid, 2 - hydroxy - 4 - methyl - 7 : 8 - (61 - hydroxybenzo)-quinoline - 41 - sulphonic acid, 2 - hydroxy - 4 - methyl - 7 : 8 - (31 - hydroxybenzo) - quinoline - 61 - sulphonic acid, 2 - hydroxy - 4 - methyl - 7 : 8 - (31 - hydroxybenzo) - quinoline - 51 - sulphonic acid and 2-hydroxy-4-methyl-7 : 8-(31-hydroxybenzo) - quinoline - 6 : 51 - disulphonic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH782062X | 1954-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB782062A true GB782062A (en) | 1957-08-28 |
Family
ID=4536302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24953/55A Expired GB782062A (en) | 1954-09-02 | 1955-08-31 | Improvements relating to quinoline compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB782062A (en) |
-
1955
- 1955-08-31 GB GB24953/55A patent/GB782062A/en not_active Expired
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