Pentanenitrile, 4,4-dimethyl-3-oxo- → ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate

HRID 1696485ノート

反応式

HRID 1696485 の反応式
Cl.[CH2:2]([O:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]([NH:17][NH2:18])[CH:8]=1)=[O:6])[CH3:3].[CH3:19][C:20]([CH3:27])([CH3:26])[C:21](=O)[CH2:22][C:23]#[N:24]>CCO.Cl>[NH2:24][C:23]1[N:17]([C:9]2[CH:8]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:18]=[C:21]([C:20]([CH3:27])([CH3:26])[CH3:19])[CH:22]=1

参加物

5

反応物 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 67271149Ethyl 3-hydrazinonaphthalene-1-carboxylate hydrochloride

生成物 1

HCID 58851682ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate収率 95.3%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

実験手順

A mixture of 3-hydrazinonaphthalene-1-carboxylic acid ethyl ester hydrochloride (1.5 g, 5.6 mmol) and 4,4-dimethyl-3-oxopentanenitrile (875 mg, 7.0 mmol) in EtOH (50 mL) and conc. HCl (5 mL) was heated at reflux overnight. After removal of the solvent, the residue was purified by column chromatography to yield ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate (1.8 g, 95% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.74 (d, J=6.3 Hz, 1H), 8.47 (s, 1H), 8.24 (s, 1H), 8.15 (d, J=6.0 Hz, 1H), 7.76 (t, J=5.7 Hz, 1H), 7.71 (t, J=5.7 Hz, 1H), 5.68 (s, 1H), 4.44 (q, J=5.4 Hz, 2H), 1.37 (t, J=5.4 Hz, 3H), 1.30 (s, 9H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customAfter removal of the solvent
  4. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-cb1abdcf015d40cf81e2b326efb74600
出典データセット
uspto-grants-2012_04
特許番号
US08163756B2

反応ノート

読み込み中…