Ethanol → HCID 15630311, compound

HRID 2164997Notes

Reaction equation

HRID 2164997 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[C:15]([O:20][CH:21]([F:23])[F:22])[CH:16]=[CH:17][CH:18]=3)[C:13](=[O:24])[C:12]([C:25]([O:27]CC)=[O:26])=[N:11]2)=[CH:6][CH:5]=1.[OH-].[Na+].C(O)C>O>[F:31][C:2]([F:1])([F:30])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:19]3[C:14](=[C:15]([O:20][CH:21]([F:23])[F:22])[CH:16]=[CH:17][CH:18]=3)[C:13](=[O:24])[C:12]([C:25]([OH:27])=[O:26])=[N:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 15630314HCID 15630314, compound

Product 1

HCID 15630311HCID 15630311, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethyl 1-(4-trifluoromethoxyphenyl)-1,4-dihydro-4-oxo-5-difluoromethoxycinnoline-3-carboxylate (200 mg) and a 1N aqueous solution of sodium hydroxide (0.93 ml) were added to a mixed solvent of ethanol (5.5 ml) and water (1.5 ml), and the resultant mixture was stirred at 70° to 80° C. for 3 hours. After being allowed to cool to room temperature, the mixture was diluted with water (50 ml), and washed with ethyl acetate (20 ml). The pH of the water layer was adjusted to pH 2 with concentrated hydrochloric acid to precipitate crystals. The precipitated crystals were collected by filtration, washed with water (5 ml) two times, and dried under reduced pressure to give 120 mg of desired 1-(4-trifluoromethoxyphenyl)-1,4-dihydro-4-oxo-5-difluoromethoxycinnoline-3-carboxylic acid (yield: 64.2%). m.p., 236.5° C.

Workup

  1. washwashed with ethyl acetate (20 ml)
  2. customto precipitate crystals
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water (5 ml) two times
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f0f52e0cdafa453e9ddd5a83dcd19598
Source dataset
uspto-grants-1990_07
Patent number
US04938794

Reaction notes

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