Methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate → Methyl 5-amino-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate

HRID 852587노트

반응식

HRID 852587 반응식
[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]

참가 물질

5

반응물 1

HCID 69360218Methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate

생성물 1

HCID 69357536Methyl 5-amino-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate수율 63%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. customThe catalyst was removed by filtration through a pad of celite and most of the solvent
  3. customremoved in vacuo
  4. customThe residue was partitioned between AcOEt and H2O
  5. customthe two layers were separated
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bf5cdfde227f49069ebdcb9cf127f445
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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