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

HRID 852587ノート

反応式

HRID 852587 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf5cdfde227f49069ebdcb9cf127f445
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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