4-Amino-3-chloro-5-methylbenzonitrile → 2-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (2-chloro-4-cyano-6-methylphenyl)amide

HRID 564741Notes

Reaction equation

HRID 564741 reaction equation
[N+](C1C=CC(O[C:11]([C:13]2[C:14]3[CH:23]=[C:22]([CH2:24][CH3:25])[O:21][C:15]=3[C:16]([O:19][CH3:20])=[N:17][CH:18]=2)=[O:12])=CC=1)([O-])=O.[NH2:26][C:27]1[C:34]([CH3:35])=[CH:33][C:30]([C:31]#[N:32])=[CH:29][C:28]=1[Cl:36]>>[Cl:36][C:28]1[CH:29]=[C:30]([C:31]#[N:32])[CH:33]=[C:34]([CH3:35])[C:27]=1[NH:26][C:11]([C:13]1[C:14]2[CH:23]=[C:22]([CH2:24][CH3:25])[O:21][C:15]=2[C:16]([O:19][CH3:20])=[N:17][CH:18]=1)=[O:12]

Participants

3

Reactant 2

HCID 27353014-Amino-3-chloro-5-methylbenzonitrileHCID 541193452-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 443653432-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (2-chloro-4-cyano-6-methylphenyl)amideYield 42.6%

Procedure

Starting from 2-ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (200 mg) and 4-amino-3-chloro-5-methylbenzonitrile (195 mg). Purification by column chromatography on silica eluting with 2% methanol in dichloromethane gave the title compound (92 mg) as a white solid.

Workup

  1. customPurification by column chromatography on silica eluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-d1a6b422098c423cb0aad4138fc6632a
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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