Methylamine → N,1-Dimethyl-5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide

HRID 21579Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([C:13](O)=[O:14])=[C:6]2[O:16][CH:17]([CH3:19])[CH3:18].[CH3:20][NH2:21].[OH-].[NH4+]>>[CH3:20][NH:21][C:13]([C:7]1[N:8]([CH3:12])[C:9]2[C:5]([C:6]=1[O:16][CH:17]([CH3:19])[CH3:18])=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)=[O:14]

Participants

Reactant 3

HCID 6329Methylamine

HCID 14923Ammonium Hydroxide

HCID 138857995-Methoxy--methyl-3-(1-methylethoxy)-1H-indole-2-carboxylic acid

Product 1

HCID 19933216N,1-Dimethyl-5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamideYield 45%

Procedure

Prepared from 5-methoxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxylic acid by the procedure of Example 1 with 40% aqueous methylamine solution substituted for ammonium hydroxide. Yield 45% after recrystallization from hexane; mp 85°-86° C.

Workup

customYield 45% after recrystallization from hexane

Sources & evidence

ORD record: ord-82db390998834a639cb2e2540efcb206
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424329

Reaction notes

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