Ethyl 3-nitro-4-(trifluoromethyl)benzoate → Ethyl 3-amino-4-(trifluoromethyl)benzoate

HRID 257576노트

반응식

HRID 257576 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-])=O.[H][H]>[Pt]=O.C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[C:15]([F:16])([F:17])[F:18])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

5

반응물 2

HCID 19783148Ethyl 3-nitro-4-(trifluoromethyl)benzoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 19783159Ethyl 3-amino-4-(trifluoromethyl)benzoate수율 77%

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매

실험 절차

A mixture of 395 mg (1.50 mmol) of ethyl 3-nitro-4-(trifluoromethyl)benzoate (from Step C), 20 mg of platinum oxide, and 6 mL of ethanol was shaken with hydrogen at 3-4 atm. for a few hours, by which time the reaction was essentially complete. The catalyst was removed by filtration, and the filtrate was concentrated to dryness. The residue was chromatographed on silica gel (elution with 25:1 hexane-EtOAc) to afford a 77% yield of the title compound as a pale yellow, gummy foam; TLC in 4:1 hexane-EtOAc; mass spectrum (EI) m/e 233 (M+). 200 MHz 1H NMR (CD3OD) δ1.36 (t, J=7.1 Hz, 3H), 4.33 (q, J=7.1 Hz, 2H), 7.26 (d, J=8 Hz, 1H), 7.44 (d, J=8 Hz, 1H) overlapping 7.47 (s, 1H).

후처리

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was chromatographed on silica gel (elution with 25:1 hexane-EtOAc)

출처 및 근거

ORD 기록
ord-b86ff7fc4ddb4d5a9165de3656719aa1
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262412

반응 노트

불러오는 중…