Ammonia → 3-Fluoro-4-methoxybenzamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5](O)=[O:6].C([N:15](CC)CC)C.C(OC(Cl)=O)C(C)C.N>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH2:15])=[O:6]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-fluoro-4-methoxybenzoic acid (400 mg, 2.4 mmol) and triethylamine (560 μl, 3.5 mmol) in tetrahydrofuran (10 mL) cooled to 0° C. was added isobutylchloroformate (320 μl, 2.4 mmol), and the mixture was stirred at 0° C. for 1 hour. The solution was warmed to room temperature and was saturated with ammonia gas, then stirred for 15 hours at room temperature. The mixture was diluted with ethyl acetate, then washed with 20% aqueous citric acid, saturated aqueous sodium bicarbonate, and brine, then dried over anhydrous sodium sulfate. Filtration and concentration afforded 280 mg, 1.7 mmol (70%) of 3-fluoro-4-(methyloxy)benzamide. MS (EI) for C8H8FNO2: 170 (MH+).
Workup
- temperatureThe solution was warmed to room temperature
- stirringstirred for 15 hours at room temperature
- washwashed with 20% aqueous citric acid, saturated aqueous sodium bicarbonate, and brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationFiltration and concentration
Sources & evidence
- ORD record
- ord-ad1ea231cfb04512a027d38567788b5e
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012956B2
Reaction notes
Loading…