Acetyl chloride → 8-Fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[C:14](Cl)(=[O:16])[CH3:15]>C(Cl)Cl>[C:14]([O:13][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([F:1])[CH:3]=1)[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2)(=[O:16])[CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Crude 8-fluoro-6-hydroxy-3,4-dihydroquinolin-2(1H)-one (0.574 g) was treated with acetyl chloride (330 mg) and TEA (0.68 mL) in DCM (8 mL) over 3 h. After aqueous work-up with EtOAc/water, the crude product was purified with a flash column chromatography to afford the desired product (382 mg) as colorless solids.
Workup
- customAfter aqueous work-up with EtOAc/water, the crude product was purified with a flash column chromatography
Sources & evidence
- ORD record
- ord-617c15a9a3f74c3982e9fd4d4f6f02df
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09433618B2
Reaction notes
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