Methanol → 1,2-Dimethyl-3-(methyliminomethyl)-1H-indole

HRID 1710550Notes

Reaction equation

HRID 1710550 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[C:3]1[CH3:13].[CH3:14][NH2:15].CO>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[N:15][CH3:14])=[C:3]1[CH3:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 5990841,2-Dimethyl-1H-indole-3-carboxaldehyde

Product 1

HCID 141422191,2-Dimethyl-3-(methyliminomethyl)-1H-indole

Procedure

To 1,2-dimethylindole-3-carboxaldehyde (11.50 g, 66.4 mmole) was added a solution of 2 M methylamine in methanol (100 mL, 200 mmole). The reaction was stirred for 4 h at RT then was concentrated to dryness to afford the crude title compound: 1H NMR (400 MHz, CDCl3) δ 8.55 (d, J=1.4 Hz, 1H), 8.16 (d, J=7.5 Hz, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.15 (t, 1H), 7.07 (t, 1H), 3.68 (s, 3H), 3.41 (s, 3H), 2.55 (s, 3H).

Workup

  1. concentrationthen was concentrated to dryness

Sources & evidence

ORD record
ord-9f8aa3d2501345fbacc768ef3d8b6e45
Source dataset
uspto-grants-2010_09
Patent number
US07790716B2

Reaction notes

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