Methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate → Methyl 5-amino-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate
Reaction equation
[F:1][C:2]1[C:11]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])=[CH:10][C:9]([N+:18]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CCO.O.[Pd]>[NH2:18][C:9]1[CH:10]=[C:11]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[C:2]([F:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
Procedure
To a solution of methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate (D140) (3.3 g, 11.7 mmol, 1 equiv) in EtOH (100 ml) and H2O (10 ml) were added NH4COOH (7.4 g, 117 mmol, 10 equiv) and 10% palladium on charcoal (50% wet, 660 mg, 10% w/w) and the resulting mixture was refluxed for 2 h then cooled to room temperature. The catalyst was removed by filtration through a pad of celite and most of the solvent removed in vacuo. The residue was partitioned between AcOEt and H2O and the two layers were separated. The organic phase was dried over MgSO4 and concentrated in vacuo to give methyl 5-amino-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate (D150) (1.85 g, 63%) as a pale yellow solid which was used in the next step without further purification. [M+H]+=253.0, RT=2.12 min.
Workup
- temperaturethe resulting mixture was refluxed for 2 h
- customThe catalyst was removed by filtration through a pad of celite and most of the solvent
- customremoved in vacuo
- customThe residue was partitioned between AcOEt and H2O
- customthe two layers were separated
- dry with materialThe organic phase was dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bf5cdfde227f49069ebdcb9cf127f445
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253198B2
Reaction notes
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