Methylamine → N,1-Dimethyl-4-methoxy-1H-indol-2-carboxamide

HRID 1920989Notes

Reaction equation

HRID 1920989 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:13]([O:15]C)=O)[N:7]2[CH3:12].[CH3:17][NH2:18]>CO>[CH3:17][NH:18][C:13]([C:6]1[N:7]([CH3:12])[C:8]2[C:4]([CH:5]=1)=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=2)=[O:15]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 4777904methyl 4-methoxy-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 22593784N,1-Dimethyl-4-methoxy-1H-indol-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
57.5 °C

Procedure

A solution of methyl 4-methoxy-1-methyl-1H-indol-2-carboxylate (1.03 g, 4.7 mmole) in 2.0 M methylamine in methanol (40 mL) was sealed in a pressure bottle and heated at 55-60° C. for 60 hr. Concentration in vacuo yielded the title compound (1.05 g, quantitative) as a white solid: MS (ES) m/e 219.2 (M+H)+.

Workup

  1. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-011a9861012940fbb2bca3edf55f80bd
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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