Water → HCID 86756021, compound

HRID 1937463Notes

Reaction equation

HRID 1937463 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:21])=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=2)[C:10](=O)[CH2:9][CH:8]1[CH3:23])=[O:6])([CH3:3])[CH3:2].Cl.[NH2:25][OH:26].C([O-])(=O)C.[Na+].O>C(O)C>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:21])=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=2)[C:10](=[N:25][OH:26])[CH2:9][CH:8]1[CH3:23])=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54498760HCID 54498760, compound

Product 1

HCID 86756021HCID 86756021, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 6-fluoro-2-methyl-4-oxo-7-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid isopropyl ester (940 mg, 2.8 mmol), hydroxylamine hydrochloride (215 mg, 3.1 mmol), and sodium acetate (254 mg, 3.1 mmol) in ethanol (20 mL) was heated at reflux for 3 h. Water (25 mL) was added, and the volatiles were removed in vacuo. Ethyl acetate (100 mL) was added, and the mixture was stirred vigorously for 10 min. The aqueous phase was separated and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound as a white foam (937 mg, ca. 100%): 1H NMR (CDCl3) δ 1.1 (d, 3H), 1.28 (d, 3H), 1.34 (d, 3H), 2.73 (dd, 1H), 3.09 (d, 1H), 5.0-5.1 (m, 2H), 7.68 (d, 1H), 7.88 (s, 1H).

Workup

  1. temperatureat reflux for 3 h
  2. customthe volatiles were removed in vacuo
  3. additionEthyl acetate (100 mL) was added
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. washThe combined organic layers were washed with brine (100 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ad01914176049e98d15bf1509f67746
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

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