Sulfuric Acid → 4-Methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Reaction equation
[C:1]([C:3]([C:10]#[N:11])=[C:4]([CH3:9])[CH:5]=[CH:6]OC)#[N:2].S(=O)(=O)(O)[OH:13]>O>[C:1]([C:3]1[C:10](=[O:13])[NH:11][CH:6]=[CH:5][C:4]=1[CH3:9])#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
The mixture of 4,4-dicyano-3-methyl-3-butenal dimethyl acetatal (1) and 1, 1-dicyano-4-methoxy-2-methyl-1,3-butadiene (2) produced by the preceding step was added to a stirred solution of concentrated sulfuric acid (1 09.8 g, 1.12 moles) at a rate so that the reaction contents did not exceed 30° C. The reaction mixture was then heated to 50° C. and held at that temperature for 1.5 hours. The reaction mixture was cooled to ambient temperature followed by the addition of water (150 mL). The product was filtered from the reaction mixture, washed with water (20 mL) and dried in a vacuum oven at 70° C. and full vacuum for 12 hours to give 40.7 g of 3-cyano-4-methyl-2-pyridone (3).
Workup
- customproduced by the preceding step
- customdid not exceed 30° C
- temperatureThe reaction mixture was cooled to ambient temperature
- filtrationThe product was filtered from the reaction mixture
- washwashed with water (20 mL)
- customdried in a vacuum oven at 70° C.
Sources & evidence
- ORD record
- ord-a1397595b60d41118d9c631c4a209fa4
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06399781B1
Reaction notes
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