Potassium tert-butoxide → Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 476776

Reaction equation

HRID 476776 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:5]([C:7](=[CH:13][NH:14][CH:15]1[CH2:17][CH2:16]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:4]2[C:3]=1[N:14]([CH:15]1[CH2:17][CH2:16]1)[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2=[O:6]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178471875HCID 178471875, compound

Product 1

HCID 13579166Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Conditions

Temperature
6 °C

Procedure

To a solution of ethyl 2-(3-chloro-2,4,5-trifluorobenzoyl)-3-cyclopropylaminoacrylate in 40 ml of dry t-butanol is added a slurry of 1.20 g (10.7 mmol) of potassium t-butoxide in 20 ml of dry t-butanol. The reaction mixture is stirred at 6° C. for eight hours, then cooled to room temperature and concentrated. The residue is dissolved in chloroform, washed with water, dried over magnesium sulfate, filtered, and concentrated to give a pale brown solid. The crude product is purified by silica gel chromatography, and eluted with 80:20 chloroform:ethyl acetate to give 1.2 g of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a pale brown solid
  9. customThe crude product is purified by silica gel chromatography
  10. washeluted with 80:20 chloroform

Sources & evidence

ORD record
ord-9b6bc155da43466689375b0b4950888a
Source dataset
uspto-grants-1989_12
Patent number
US04885386

Linked notes

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