Reaction equation
CC([O-])(C)C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[CH3:13][C:14](=O)[CH:15]=[CH:16][CH2:17][CH3:18].O=O.Cl>CS(C)=O.O>[CH2:17]([C:16]1[CH:15]=[C:14]([CH3:13])[NH:12][C:10](=[O:11])[C:9]=1[C:7]#[N:8])[CH3:18]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of t-BuOK (22.85 g, 204.08 mmol) and cyanoacetamide (18.8 g, 224.1 mmol) in DMSO (300 mL) was added hex-3-en-2-one (20 g, 204.08 mmol) under argon atmosphere at room temperature. The reaction mixture was then stirred at room temperature for 30 min and then added additional t-BuOK (68.5 g, 612.05 mmol) was added. Argon gas was displaced by oxygen gas and the mixture stirred for 48 hrs at room temperature in presence of oxygen. Reaction was monitored by TLC. The reaction mixture was cooled to 0° C. and diluted with water (100 mL) followed by 4 N HCl (120 mL). The mixture was stirred for 15 min and the resulting solid was filtered. The solid was washed with water (1 L) and dried to afford the title compound, 4-ethyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile (10.5 g, 31%), as an off white solid. 1H NMR (CDCl3 400 MHz): δ ppm 1.148-1.185 (t, 3H, J=7.4 Hz), 2.237 (s, 3H), 2.557-2.614 (m, 2H), 6.211 (s, 1H), 12.330 (broad s, 1H). MS(ES) [M+H]+ 161.06.
Workup
- additionwas added
- customReaction
- temperatureThe reaction mixture was cooled to 0° C.
- stirringThe mixture was stirred for 15 min
- filtrationthe resulting solid was filtered
- washThe solid was washed with water (1 L)
- customdried
Sources & evidence
- ORD record
- ord-5d9e9705125c4bf086a84d72e1ef96d7
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446041B2
Linked notes
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