Sodium Hydroxide → 8-Fluoro-6-hydroxy-3,4-dihydroquinolin-2(1H)-one

HRID 77439Notes

Reaction equation

HRID 77439 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[NH:11][C:10](=[O:16])[CH2:9][CH2:8]2)(=O)C.[OH-].[Na+]>CO>[F:15][C:13]1[CH:14]=[C:5]([OH:4])[CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:16])[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 99911448-Fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate

Product 1

HCID 103750488-Fluoro-6-hydroxy-3,4-dihydroquinolin-2(1H)-oneYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate (1.3 g, 5.82 mmol) in MeOH (50 mL) at room temperature was added 1N NaOH (11.65 mL, 11.65 mmol). The reaction mixture was stirred at room temperature overnight, then concentrated to a yellow oil. This was diluted with water and acidified with conc. HCl to pH 1. The precipitate was collected by filtration, washed with water, and recrystallized from MeOH/water to give 8-fluoro-6-hydroxy-3,4-dihydroquinolin-2(1H)-one as a white solid (0.46 g, 44%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 6.57-6.48 (m, 2H), 2.93 (s, 2H), 2.56 (dd, J=7.9, 6.9 Hz, 2H). LCMS: R.T.=1.125 min; [M+H]+=182.1.

Workup

  1. concentrationconcentrated to a yellow oil
  2. additionThis was diluted with water
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customrecrystallized from MeOH/water

Sources & evidence

ORD record
ord-22cd78c0d7444172ab5085b15e8d20df
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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