Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-(tert-butyl)-1-(quinolin-3-yl)-1H-pyrazol-5-amine

HRID 1696479ノート

反応式

HRID 1696479 の反応式
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:12][NH2:13])[CH:3]=1.[CH3:14][C:15]([CH3:22])([CH3:21])[C:16](=O)[CH2:17][C:18]#[N:19]>CCO.Cl>[C:15]([C:16]1[CH:17]=[C:18]([NH2:19])[N:12]([C:4]2[CH:3]=[N:2][C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:13]=1)([CH3:22])([CH3:21])[CH3:14]

参加物

5

反応物 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 204856003-Hydrazinylquinoline hydrochloride

生成物 1

HCID 588514923-(tert-butyl)-1-(quinolin-3-yl)-1H-pyrazol-5-amine収率 55%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

実験手順

A mixture of 1-(quinolin-3-yl)hydrazine hydrochloride (4 g, 20.5 mmol) and 4,4-dimethyl-3-oxo-pentanenitrile (3.6 g, 30 mol) 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 3-t-butyl-1-(quinolin-3-yl)-1H-pyrazol-5-amine (3.0 g, 55% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.16 (d, J=2.4 Hz, 1H), 8.44 (d, J=2.4 Hz, 1H), 8.03 (s, 1H), 8.00 (s, 1H), 7.72 (t, J=7.2 Hz, 1H), 7.64 (t, J=7.2 Hz, 1H), 5.72 (s, 1H), 5.45 (s, 3H), 1.23 (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-ff2f74685b704055a7b055f5a3be18b2
出典データセット
uspto-grants-2012_04
特許番号
US08163756B2

反応ノート

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