Ammonia → 2-(5-Dimethylaminomethyl-2-methyl-benzofuran-3-yl)-acetamide

HRID 402911Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][C:6]1[C:10]2[CH:11]=[C:12]([CH2:15][N:16]([CH3:18])[CH3:17])[CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[CH3:19])C.[NH3:21]>CO>[CH3:17][N:16]([CH2:15][C:12]1[CH:13]=[CH:14][C:9]2[O:8][C:7]([CH3:19])=[C:6]([CH2:5][C:4]([NH2:21])=[O:3])[C:10]=2[CH:11]=1)[CH3:18]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of (5-dimethylaminomethyl-2-methyl-benzofuran-3-yl)-acetic acid ethyl ester (744 mg, 2.70 mmol) in a mixture of methanol (5 mL) and liquid ammonia (40 mL) is stirred for 3 days in an autoclave at 70° C. After careful evaporation of the ammonia, the remaining solvent is evaporated in vacuo to afford the title compound as beige solid (662 mg, 2.42 mmol, 90%). 1H NMR (400 MHz, DMSO-d6, 298 K): δ=7.48 (bs, 1H), 7.42 (s, 1H), 7.36 (d, J=8.6 Hz, 1H), 7.11 (d, J=8.6 Hz, 1H), 6.93 (bs, 1H), 3.45 (s, 2H), 3.38 (s, 2H), 2.38 (s, 3H), 2.15 (s, 6H). MS (ES+): 247 (M(C16H14O4)+H)+.

Workup

customAfter careful evaporation of the ammonia
customthe remaining solvent is evaporated in vacuo

Sources & evidence

ORD record: ord-7d722eb3c0ee426b975bc1a5be529bea
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742132B2

Reaction notes

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