Sulfuryl chloride → 5-chloro-6-methoxy-4-methyl-1H-quinolin-2-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[C:6]2[CH3:14].S(Cl)([Cl:18])(=O)=O>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:4]([Cl:18])=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[C:6]2[CH3:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
In a 250 ml, three-necked round bottom flask equipped with a mechanical stirrer, thermowatch, and addition funnel was placed glacial acetic acid (125 ml) and 6-methoxy-4-methyl-2-quinolone (15.78 g, 0.0834 moles). This was heated to 70° C., then a solution of sulfuryl chloride (13.5 g, 0.100 moles) and glacial acetic acid (10 ml) was added over 50 minutes. Reaction temperature held between 70-75° C. and product precipitated from solution about one third through the addition. The slurry was stirred for 15 minutes , then cooled to ambient temperature. Product was isolated by suction filtration followed by two 20 ml washes with acetic acid and one 50 ml wash with ethanol. Air dried yield is 17.9 g; purity by HPLC is 76.6 area % (contains 9.8% starting material and 12.8% over chlorinated product)
Workup
- customIn a 250 ml, three-necked round bottom flask equipped with a mechanical stirrer
- additionthermowatch, and addition funnel
- customReaction temperature
- customheld between 70-75° C.
- customproduct precipitated from solution about one third through the addition
- temperaturecooled to ambient temperature
- customProduct was isolated by suction filtration
- washwith acetic acid and one 50 ml wash with ethanol
- customAir dried yield is 17.9 g
Sources & evidence
- ORD record
- ord-4dd8005190df40e0969d1e5c72e11b3f
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479660B1
Reaction notes
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