Acetyl chloride → 8-Fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate

HRID 55848Notes

Reaction equation

HRID 55848 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

HCID 6367Acetyl chlorideHCID 103750488-Fluoro-6-hydroxy-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 99911448-Fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetateYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. 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

Loading…