Hydrazine hydrate (1:1) → 4-(Pyridin-2-yl)-1H-pyrazole-3,5-diamine

HRID 490109

반응식

HRID 490109 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:10]#[N:11])[C:8]#[N:9].O.[NH2:13][NH2:14]>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:10]([NH2:11])=[N:13][NH:14][C:8]=1[NH2:9]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 102409162-Pyridylmalononitrile

생성물 1

HCID 576745884-(Pyridin-2-yl)-1H-pyrazole-3,5-diamine수율 52.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-pyridin-2-yl-malononitrile (0.65 g, 4.59 mmol) and hydrazine hydrate (225 μL, 4.59 mmol) in EtOH (5 mL) was heated to reflux and stirred for 16 hours. The reaction mixture was cooled down to room temperature and filtered. The resulting solid was washed with Et2O to provide the title compound as a light tan solid (0.42 g, 52%). The filtrate was evaporated to dryness and purified by silica gel chromatography eluting with NH4OH:MeOH:CH2Cl2 (0.5:5:95) to give a further 63.3 mg (8%) of the desired product. MS (ES+) 176, (ES−) 174. δH (DMSO-d6) 5.45 (4H, br s), 6.98 (1H, t), 7.57 (1H, d), 7.69 (1H, t), 8.46 (1H, d), 10.55 (1H, br s).

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. washThe resulting solid was washed with Et2O

출처 및 근거

ORD 기록
ord-aef4521d22c647d0bbaad0dfb900de50
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528138B2

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