Potassium Carbonate → HCID 14146226, compound

HRID 444796Notes

Reaction equation

HRID 444796 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([O:13][CH2:14][C:15]4([CH2:17][CH2:16]4)[N:8]3[CH:7]=[C:6]([C:18]([O:20]CC)=[O:19])[C:5]2=[O:23])[C:11]=1[F:12].C([O-])([O-])=O.[K+].[K+]>CCO.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([O:13][CH2:14][C:15]4([CH2:17][CH2:16]4)[N:8]3[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:23])[C:11]=1[F:12]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14146225HCID 14146225, compound

Product 1

HCID 14146226HCID 14146226, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of ethyl 9,10-difluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1′-cyclopropane]-6-carboxylate (1.3 g, 4 mmol) in EtOH/water (50:50 v/v, 55 mL) was added K2CO3 powder (1.65 g, 12 mmol) and the mixture was heated under reflux for 2 h. The solvent was removed to dryness. The remaining solid was acidified to pH6 by using 2N acetic acid. A precipitate formed and was collected by filtration, washed with water and then dried to give the title compound (0.656 g, 2.24 mmol as a light yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 1.29 (2H, t), 1.8 (2H, t), 4.56 (2H, s), 7.84 (1H, m), 8.51 (1H, s), 14.3 (1H, b). MS (EP) m/z: 294 (M++1). (Calcd for C14H9F2NO4, 293.22)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. customThe solvent was removed to dryness
  4. customA precipitate formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-77bf220fdd8042a39c18c90ce58aca2a
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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