Ethanol → ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate

HRID 1392317

반응식

HRID 1392317 반응식
Cl.[NH:2]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])[NH2:3].[CH3:13][C:14]([CH3:21])([CH3:20])[C:15](=O)[CH2:16][C:17]#[N:18].[CH2:22](O)[CH3:23]>>[CH2:22]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N:2]2[C:17]([NH2:18])=[CH:16][C:15]([C:14]([CH3:21])([CH3:20])[CH3:13])=[N:3]2)[CH:5]=1)[CH3:23].[NH2:18][C:17]1[N:2]([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[C:7]([OH:9])=[O:8])[N:3]=[C:15]([C:14]([CH3:21])([CH3:20])[CH3:13])[CH:16]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 128918633-Hydrazinobenzoic acid hydrochloride

생성물 2

HCID 218672843-(3-tert-butyl-5-amino-1H-pyrazol-1-yl)benzoic acid수율 36%HCID 21867322ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate수율 40%

실험 절차

A mixture of 3-hydrazino-benzoic acid hydrochloride (200 g, 1.06 mol) and 4,4-dimethyl-3-oxo-pentanenitrile (146 g, 1.167 mol) in ethanol (2 L) was heated to reflux overnight. The reaction solution was evaporated under reduced pressure. The residue was purified by column chromatography to give 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid ethyl ester (116 g, 40%) as a white solid together with 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid (93 g, 36%). 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid and ethyl ester: 1H NMR (DMSO-d6): 8.09 (s, 1 H), 8.05 (brd, J=8.0 Hz, 1 H), 7.87 (br d, J=8.0 Hz, 1 H), 7.71 (t, J=8.0 Hz, 1 H), 5.64 (s, 1 H), 4.35 (q, J=7.2 Hz, 2 H), 1.34 (t, J=7.2 Hz, 3 H), 1.28 (s, 9H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe reaction solution was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-34fa235c70484754a807d4283b3bd9d9
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342037B2

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