Ethanol → 4-Amino-9-(4-methoxyphenyl)methyl-2-methyl-9H-pyrido[2,3-b]indole-3-carboxylic acid, ethyl ester

HRID 1710050Notes

Reaction equation

HRID 1710050 reaction equation
[NH2:1][C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:6]=2[N:5]=[C:4]([CH3:24])[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C1(C)C=CC=CC=1.C(O)C>C1C=CC=CC=1>[NH2:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:6]=2[N:5]=[C:4]([CH3:24])[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

6

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 867441794-Amino-9-(4-methoxyphenyl)methyl-2-methyl-5,6,7,8-tetrahydro-9H-pyrido[2,3-b]indole-3-carboxylic acid, ethyl ester

Product 1

HCID 867441804-Amino-9-(4-methoxyphenyl)methyl-2-methyl-9H-pyrido[2,3-b]indole-3-carboxylic acid, ethyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The title compound was prepared in 73% yield from 4-amino-9-(4-methoxyphenyl)methyl-2-methyl-5,6,7,8-tetrahydro-9H-pyrido[2,3-b]indole-3-carboxylic acid, ethyl ester (D8) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in a procedure similar to Description 7, using benzene as solvent instead of toluene. Product was obtained as white crystals from ethanol.

Sources & evidence

ORD record
ord-0a4180e9915844eab76da7e547b9a5db
Source dataset
uspto-grants-1990_08
Patent number
US04952584

Reaction notes

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