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

HRID 1050438Notes

Reaction equation

HRID 1050438 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-09bee15e87fc49b4bea8223025bf02fb
Source dataset
uspto-grants-2016_07
Patent number
US09382234B2

Reaction notes

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