Methylamine → 6-methoxy-N,1-dimethyl-1H-indole-3-carboxamide

HRID 985210Notes

Reaction equation

HRID 985210 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:13]([OH:15])=O)=[CH:8][N:9]2[CH3:12])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH3:22][NH2:23]>>[CH3:22][NH:23][C:13]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH3:12])[CH:8]=1)=[O:15]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 221434786-methoxy-1-methyl-1H-indole-3-carboxylic acid

Product 1

HCID 221434906-methoxy-N,1-dimethyl-1H-indole-3-carboxamideYield 83.8%

Procedure

This material was prepared from 6-methoxy-1-methyl-indole-3-carboxylic acid 16b (515 mg, 2.5 mmole), oxalyl chloride (0.9 ml, 12.6 mmole) and methylamine (7.5 mmole) in a manner as previously described for example 16d to give 457 mg of a pale brown solid (83%). 1H NMR (CD3OD) δ7.83 (1H, d, J=8.7 Hz), 7.51 (1H, s), 6.81 (1H, d, J=2.3 Hz), 6.72 (1H, dd, J=2.3, 8.7 Hz), 3.75 (3H, s), 3.67 (3H, s), 2.80 (3H, s); ESIMS (MH+): 219.05.

Sources & evidence

ORD record
ord-66a4efc691484c56ae55f314f9de9303
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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