4-Amino-3,5-dichlorobenzonitrile → 2-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (2,6-dichloro-4-cyanophenyl)amide

HRID 564738

Reaction equation

HRID 564738 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]([Cl:35])=[CH:33][C:30]([C:31]#[N:32])=[CH:29][C:28]=1[Cl:36]>>[Cl:35][C:34]1[CH:33]=[C:30]([C:31]#[N:32])[CH:29]=[C:28]([Cl:36])[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 5227064-Amino-3,5-dichlorobenzonitrileHCID 541193452-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 867561902-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (2,6-dichloro-4-cyanophenyl)amideYield 44.7%

Procedure

Starting from 2-ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.10 g) and 4-amino-3,5-dichlorobenzonitrile (0.12 g). Purification by column chromatography on silica with 20% then 30% then 50% ethyl acetate in hexane to give the title compound (0.051 g) as a cream solid.

Workup

  1. customPurification by column chromatography on silica with 20%

Sources & evidence

ORD record
ord-a03d1dc6e8784a9fb0c11c71e9cbe82b
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Linked notes

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