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

HRID 492004

反応式

HRID 492004 の反応式
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

参加物

5

反応物 3

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

生成物 2

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

実験手順

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, 1H), 8.05 (brd, J=8.0 Hz, 1H), 7.87 (br d, J=8.0 Hz, 1H), 7.71 (t, J=8.0 Hz, 1H), 5.64 (s, 1H), 4.35 (q, J=7.2 Hz, 2H), 1.34 (t, J=7.2 Hz, 3H), 1.28 (s, 9H).

後処理

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

出典と根拠

ORDレコード
ord-6ab6eb51d56243dba52455e00eafc2e4
出典データセット
uspto-grants-2009_05
特許番号
US07531566B2

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