Ammonium Hydroxide → 1H-Indole-2-carboxamide

HRID 1601059Notes

Reaction equation

HRID 1601059 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]CC)=O.[OH-].[NH4+:16]>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH2:16])=[O:12]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 5948321H-Indole-2-carboxamide

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl indole-2-carboxylate (5 g, 26.5 mmol) and ammonium hydroxide (30 mL) was heated at 80° C. in a sealed glass vessel overnight. The reaction was cooled and the title compound (3.06 g, 73%) was collected by filtration as a colorless solid: 1H NMR (400 MHz, DMSO-d6) δ 7.95 (br, 1H), 7.61 (d, 1H), 7.41 (d, 1H), 7.36 (br, 1H), 7.12, (t, 1H), 7.01 (t, 1H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe title compound (3.06 g, 73%) was collected by filtration as a colorless solid

Sources & evidence

ORD record
ord-1eb2ab351a0d4fa4aea71561aab9f3b3
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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