Ammonia → 4-Acetylamino-2,3-dihydrobenzofuran-7-carboxylic acid amide
Reaction equation
[NH3:1].C[O:3][C:4]([C:6]1[C:14]2[O:13][CH2:12][CH2:11][C:10]=2[C:9]([NH:15][C:16](=[O:18])[CH3:17])=[CH:8][CH:7]=1)=O>CO>[C:16]([NH:15][C:9]1[C:10]2[CH2:11][CH2:12][O:13][C:14]=2[C:6]([C:4]([NH2:1])=[O:3])=[CH:7][CH:8]=1)(=[O:18])[CH3:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Ammonia gas was bubbled through a solution of 4-acetylamino-2,3-dihydro-benzofuran-7-carboxylic acid methyl ester (12 g, 51 mmol, prepared as described in Takuji Kakigami et al, Chem. Pharm. Bull, 46 (1), 42-52, (1998)) in CH3OH (200 mL) in a pressure bottle at 0-5° C. until the solution was saturated. The bottle was sealed and stirred at 60° C. overnight. After cooling to 0-5° C., the reaction mixture was charged one more time with NH3 gas, then the sealed bottle stirred at 60° C. for another 24 h. After cooling to rt, white precipitates were collected by filtration, and dried under vacuum to furnish the title compound (10.5 g) as a white solid.
Workup
- customThe bottle was sealed
- temperatureAfter cooling to 0-5° C.
- stirringthe sealed bottle stirred at 60° C. for another 24 h
- temperatureAfter cooling to rt
- customwhite precipitates
- filtrationwere collected by filtration
- customdried under vacuum
Sources & evidence
- ORD record
- ord-43af2e7ccc574b1693bcd0e881972425
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405234B2
Reaction notes
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