Methylhydrazine → 1-Methyl-3-Pyridin-2-Yl-1H-Pyrazol-5-Amine

HRID 1748794노트

반응식

HRID 1748794 반응식
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:3][C:4]#[N:5].[CH3:12][NH:13][NH2:14]>C(O)C>[CH3:12][N:13]1[C:4]([NH2:5])=[CH:3][C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:14]1

참가 물질

4

반응물 2

HCID 6061MethylhydrazineHCID 115718233-Oxo-3-(pyridin-2-yl)propanenitrile

생성물 1

HCID 133248371-Methyl-3-Pyridin-2-Yl-1H-Pyrazol-5-Amine수율 63%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of crude 3-oxo-3-(2-pyridyl)propanenitrile (48.6 g, 331 mmol) in ethanol (500 mL) was added methyl hydrazine (25 g, 543 mmol). The resulting mixture was stirred for about 30 min at rt and then heated at about 75° C. for about 18 h. After cooling to rt the reaction mixture was concentrated in vacuo. The residue was treated with toluene (300 mL). The formed solid was collected by filtration and washed with toluene (150 mL). The solid was dried under vacuum to give 1-methyl-3-(2-pyridyl)pyrazol-5-amine (36.2 g, 208 mmol, 63%). 1H-NMR (CDCl3, Bruker 400 MHz) δ 3.62 (3H, s); 5.34 (2H, br s); 5.90 (1H, s); 7.21 (1H, m); 7.73 (1H, dt, J=10 Hz, 2 Hz); 7.83 (1H, dt, J=10 Hz, 1 Hz); 8.51 (1H, dt, J=6 Hz, 2 Hz).

후처리

  1. temperatureheated at about 75° C. for about 18 h
  2. temperatureAfter cooling to rt the reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionThe residue was treated with toluene (300 mL)
  5. filtrationThe formed solid was collected by filtration
  6. washwashed with toluene (150 mL)
  7. customThe solid was dried under vacuum

출처 및 근거

ORD 기록
ord-3f82351a0a174617aff690a16ec2873f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150592B2

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