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

HRID 1050438ノート

反応式

HRID 1050438 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 131485354-Hydroxy-2,6-dimethylpyridine-3-carbonitrile収率 19.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-09bee15e87fc49b4bea8223025bf02fb
出典データセット
uspto-grants-2016_07
特許番号
US09382234B2

反応ノート

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