GB822736A - New indoles and process for their manufacture - Google Patents
New indoles and process for their manufactureInfo
- Publication number
- GB822736A GB822736A GB22294/56A GB2229456A GB822736A GB 822736 A GB822736 A GB 822736A GB 22294/56 A GB22294/56 A GB 22294/56A GB 2229456 A GB2229456 A GB 2229456A GB 822736 A GB822736 A GB 822736A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- indole
- salts
- methyl
- benzyl
- 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
- 150000002475 indoles Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- KRKOUYGRFMARHC-UHFFFAOYSA-N 1-benzylindol-2-amine Chemical compound NC1=CC2=CC=CC=C2N1CC1=CC=CC=C1 KRKOUYGRFMARHC-UHFFFAOYSA-N 0.000 abstract 1
- LSZQSKSNLUSAHW-UHFFFAOYSA-N 1-ethylindol-2-amine Chemical compound NC=1N(C2=CC=CC=C2C1)CC LSZQSKSNLUSAHW-UHFFFAOYSA-N 0.000 abstract 1
- PZZCRWCCMIBFPB-UHFFFAOYSA-N 1-methyl-5-phenylmethoxyindol-2-amine Chemical compound CN1C(=CC2=CC(=CC=C12)OCC1=CC=CC=C1)N PZZCRWCCMIBFPB-UHFFFAOYSA-N 0.000 abstract 1
- SZFPOMLSQTZGNM-UHFFFAOYSA-N 1-methylindol-2-amine Chemical compound C1=CC=C2N(C)C(N)=CC2=C1 SZFPOMLSQTZGNM-UHFFFAOYSA-N 0.000 abstract 1
- ZFDZPKNZFAHZCY-UHFFFAOYSA-N 2-(2-amino-5-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(N)C(CC#N)=C1 ZFDZPKNZFAHZCY-UHFFFAOYSA-N 0.000 abstract 1
- WQOMHMXXKKRUFU-UHFFFAOYSA-N 2-(2-amino-5-phenylmethoxyphenyl)acetonitrile Chemical compound NC1=C(CC#N)C=C(C=C1)OCC1=CC=CC=C1 WQOMHMXXKKRUFU-UHFFFAOYSA-N 0.000 abstract 1
- LMDPYYUISNUGGT-UHFFFAOYSA-N 2-(2-aminophenyl)acetonitrile Chemical class NC1=CC=CC=C1CC#N LMDPYYUISNUGGT-UHFFFAOYSA-N 0.000 abstract 1
- NFNHNFXXPSLAPI-UHFFFAOYSA-N 2-amino-1-methylindol-5-ol Chemical compound CN1C(=CC2=CC(=CC=C12)O)N NFNHNFXXPSLAPI-UHFFFAOYSA-N 0.000 abstract 1
- BABQUGZTENNQSB-UHFFFAOYSA-N 5-methoxy-1-methylindol-2-amine Chemical compound COC1=CC=C2N(C)C(N)=CC2=C1 BABQUGZTENNQSB-UHFFFAOYSA-N 0.000 abstract 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract 1
- -1 and R1 is H Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- YMOPFJHCVLXQEO-UHFFFAOYSA-N ethyl 2-(2-aminoindol-1-yl)acetate Chemical compound C(=O)(OCC)CN1C(=CC2=CC=CC=C12)N YMOPFJHCVLXQEO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention comprises indoles of the formula <FORM:0822736/IV (a)/1> where R is alkyl, substituted alkyl or aralkyl, and R1 is H, alkyl, hydroxyl or substituted hydroxyl, and salts thereof. The salts are obtained by reacting an amino-nitrile <FORM:0822736/IV (a)/2> with a suitable compound RX, where X is e.g. halogen, benzenesulphonate or p-toluenesulphonate, if desired in the presence of a solvent. The salts can be converted into the free bases from which other salts may be obtained. Examples show the production of 1-methyl-2-amino-indole, 1-benzyl-2-amino-indole, 1-carbethoxymethyl - 2 - amino - indole, 1 - ethyl - 2-amino - indole, 1 - methyl - 2 - amino - 5 - methoxyindole and 1-methyl-2-amino-5-benzyloxy-indole, from which 1-methyl-2-amino-5-hydroxyindole can be obtained by hydrogenolysis. 2-Amino-benzyl cyanides can be made by reducing the corresponding 2-nitro compounds, the preparation of 2-amino-5-methoxy-benzyl cyanide and 2-amino-5-benzyloxy-benzyl cyanide being mentioned.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH822736X | 1955-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB822736A true GB822736A (en) | 1959-10-28 |
Family
ID=4539605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22294/56A Expired GB822736A (en) | 1955-07-18 | 1956-07-18 | New indoles and process for their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB822736A (en) |
-
1956
- 1956-07-18 GB GB22294/56A patent/GB822736A/en not_active Expired
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