Methyl 4-cyano-2-fluoro-5-nitrobenzoate → Benzoic acid, 5-amino-4-cyano-2-fluoro-, methyl ester

HRID 906170ノート

反応式

HRID 906170 の反応式
[C:1]([C:3]1[C:12]([N+:13]([O-])=O)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:16])[CH:4]=1)#[N:2]>C(O)(=O)C.[Fe]>[NH2:13][C:12]1[C:3]([C:1]#[N:2])=[CH:4][C:5]([F:16])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

参加物

4

反応物 1

HCID 67403309Methyl 4-cyano-2-fluoro-5-nitrobenzoate

生成物 1

HCID 67403793Benzoic acid, 5-amino-4-cyano-2-fluoro-, methyl ester収率 68%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

実験手順

To a solution of methyl 4-cyano-2-fluoro-5-nitrobenzoate (785 mg, 3.5 mmol) in acetic acid (15 mL) was added iron powder (1.17 g, 21.0 mmol). The mixture was stirred vigorously at room temperature for 2 h. Insoluble solids were then removed by filtration through celite. Water was added to the filtrate and the aqueous mixture was extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (30% ethyl acetate in hexanes) to provide methyl 5-amino-4-cyano-2-fluorobenzoate (463 mg, 2.38 mmol, 68% yield). 1H NMR (400 MHz, CDCl3): 7.30 (d, 1H), 7.19 (d, 1H), 4.41 (br s, 2H), 3.94 (s, 3H); MS (EI) for C9H7FN2O2: 193 (M−H).

後処理

  1. customInsoluble solids were then removed by filtration through celite
  2. additionWater was added to the filtrate
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-a15f78c5d8eb4aeb911e16bcaddb7cb5
出典データセット
uspto-grants-2011_09
特許番号
US08012956B2

反応ノート

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