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

HRID 257576

反応式

HRID 257576 の反応式
[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]

参加物

5

反応物 2

HCID 19783148Ethyl 3-nitro-4-(trifluoromethyl)benzoateHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b86ff7fc4ddb4d5a9165de3656719aa1
出典データセット
uspto-grants-1993_11
特許番号
US05262412

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