Acetic Acid → 1,4-Dimethyl-2-quinolone
Reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9]=[C:10]1O[C:12](=[O:13])[CH2:11]1.C(O)(=O)C.S(=O)(=O)(O)O>C(OCC)(=O)C.O>[CH3:1][N:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:10]([CH3:9])=[CH:11][C:12]1=[O:13]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
The starting 1,2-dihydro-1,4-dimethyl-2-quinolone (3) is prepared by first conjugating N-methylaniline with diketene, followed by an acid cyclization of the amide intermediate. Thus 10.0 g (0.12 moles) of diketene is added dropwise to 10.7 g (0.1 moles) of N-methylaniline and the reaction is heated at 100 ° C. for an additional 30 minutes. To the resulting mixture is added 30 mL of acetic acid and 30 mL of sulfuric acid, and the mixture is heated at 50 ° C. overnight. The reaction is worked up with water and ethyl acetate and purified on a silica gel column to yield 9.5 g of the desired product.
Workup
- temperaturethe mixture is heated at 50 ° C. overnight
- custompurified on a silica gel column
Sources & evidence
- ORD record
- ord-135e9c84e59248309a99819ebee41732
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05436134
Reaction notes
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