Ethyl 6-cyano-1H-indole-2-carboxylate → 6-Cyano-1H-indole-2-carboxamide

Reaction equation

[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14]CC)=O)[NH:9]2)=[CH:5][CH:4]=1)#[N:2].[NH3:17].CO>>[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([NH2:17])=[O:14])[NH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

Reactant 2

HCID 4715002Ethyl 6-cyano-1H-indole-2-carboxylate

HCID 21705897Ammonia methanol

Product 1

HCID 670957536-Cyano-1H-indole-2-carboxamideYield 88.6%

Procedure

Treat 6-cyano-1H-indole-2-carboxylic acid ethyl ester 5a (m=0, 1.0 g, 4.67 mmol) with 7 N NH3/MeOH as described in General Procedure IV to afford the title compound as an ivory colored solid (766 mg, 88.6%), mp 241-242° C.; 1H NMR (DMSO-d6) δ 11.5 (brs, 1H), 8.16 (brs, 1H), 7.83 (s, 1H), 7.80 (d, 1H, J=8.0 Hz), 7.58 (brs, 1H), 7.35 (d, 1H, J=8.0 Hz), 7.23 (s, 1H).

Sources & evidence

ORD record: ord-81327bbc2b934d938c2f05fb61667ef7
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923466B2

Reaction notes

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