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

HRID 906170노트

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HRID 906170 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a15f78c5d8eb4aeb911e16bcaddb7cb5
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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