m-Chloroperbenzoic acid → 8-Fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate

HRID 77438Notes

Reaction equation

HRID 77438 reaction equation
C([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([F:14])[CH:13]=1)[NH:10][C:9](=[O:15])[CH2:8][CH2:7]2)(=O)C.ClC1C=CC=[C:19]([C:23]([O:25]O)=[O:24])C=1>C(Cl)(Cl)Cl>[C:23]([O:25][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([F:14])[CH:13]=1)[NH:10][C:9](=[O:15])[CH2:8][CH2:7]2)(=[O:24])[CH3:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 100132396-Acetyl-8-fluoro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 99911448-Fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetateYield 75.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of 6-acetyl-8-fluoro-3,4-dihydroquinolin-2(1H)-one (1.6 g, 7.72 mmol) in CHCl3 (100 mL) at room temperature was added in portions m-chloroperbenzoic acid (2.077 g, 9.27 mmol). The reaction mixture was stirred at reflux for 18 h, then cooled to room temperature and quenched with saturated sodium bicarbonate solution. The reaction was extracted with DCM (3×100 mL). The combined organic layers were dried over MgSO4 and concentrated under vacuum to a yellow oil. This was purified by column chromatography on silica gel using 1% MeOH in DCM to give 8-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate as a white foam (1.3 g, 75%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.28 (s, 1H), 6.84-6.72 (m, 1H), 2.77-2.54 (m, 2H), 2.45-2.21 (m, 2H), 1.62 (s, 3H). LCMS: R.T.=1.382 min; [M+H]+=224.0.

Workup

  1. temperatureat reflux for 18 h
  2. customquenched with saturated sodium bicarbonate solution
  3. extractionThe reaction was extracted with DCM (3×100 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated under vacuum to a yellow oil
  6. customThis was purified by column chromatography on silica gel using 1% MeOH in DCM

Sources & evidence

ORD record
ord-89bb55dffd514f10bdae0b6bc712a1c1
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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