3-Amino-2-butenenitrile → 4-Hydroxy-2,6-dimethylpyridine-3-carbonitrile

HRID 1050438노트

반응식

HRID 1050438 반응식
[NH2:1][C:2]([CH3:6])=[CH:3][C:4]#[N:5].CC1(C)[O:13][C:12](=O)[CH:11]=[C:10]([CH3:15])O1>CCOC(C)=O>[CH3:6][C:2]1[NH:1][C:10]([CH3:15])=[CH:11][C:12](=[O:13])[C:3]=1[C:4]#[N:5]

참가 물질

4

반응물 2

HCID 706993-Amino-2-butenenitrileHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

생성물 1

HCID 131485354-Hydroxy-2,6-dimethylpyridine-3-carbonitrile수율 19.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

A 250 mL round bottom flask was charged with 3-aminobut-2-enenitrile (10.00 g, 122 mmol), 2,2,6-trimethyl-4H-1,3-dioxin-4-one (32.4 mL, 244 mmol), and a magnetic stir bar. The flask was equipped with a reflux condenser and a CaCl2 tube and the reaction mixture was heated at 130° C. for 1 h. The reaction was allowed to cool room temperature and was diluted with EtOAc (100 mL). The solid that formed was collected, washed with EtOAc (20 mL), and dried to give 2,6-dimethyl-4-oxo-1,4-dihydropyridine-3-carbonitrile (3.5 g, 23.62 mmol, 19.4% yield) as a beige soild. 1H NMR (400 MHz, DMSO-d6) δ 11.94 (br. s., 1H), 6.04 (s, 1H), 2.41 (s, 3H), 2.21 (s, 3H). MS(ES) [M+H]+ 148.9.

후처리

  1. customThe flask was equipped with a reflux condenser and a CaCl2 tube
  2. temperatureto cool room temperature
  3. customThe solid that formed
  4. customwas collected
  5. washwashed with EtOAc (20 mL)
  6. customdried

출처 및 근거

ORD 기록
ord-09bee15e87fc49b4bea8223025bf02fb
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382234B2

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