Ethanol → HCID 10406690, compound

HRID 2352132Notes

Reaction equation

HRID 2352132 reaction equation
[F:1][C:2]([F:28])([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[C:15]([F:20])[CH:16]=[CH:17][CH:18]=3)[C:13](=[O:21])[C:12]([C:22]([O:24]CC)=[O:23])=[N:11]2)=[CH:6][CH:5]=1.[OH-].[K+].C(O)C>O>[F:28][C:2]([F:1])([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[C:15]([F:20])[CH:16]=[CH:17][CH:18]=3)[C:13](=[O:21])[C:12]([C:22]([OH:24])=[O:23])=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 14678553HCID 14678553, compound

Product 1

HCID 10406690HCID 10406690, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethyl 1-(4-trifluoromethoxyphenyl)-1,4-dihydro-4-oxo-5-fluorocinnoline-3-carboxylate (2.31 g) and potassium hydoxide (0.67 g) were added to a mixed solvent of ethanol (24 ml) and water (6 ml), and the resultant mixture was stirred at 60° to 70° C. for 7 hours. After being allowed to cool to room temperature, the mixture was diluted with water (100 ml), and washed with diethyl ether (30 ml). The water layer was neutralized with concentrated hydrochloric acid to pH 2 to precipitate crystals. The precipitated crystals was collected by filtration, washed two times with water (20 ml), and dried under reduced pressure to give 2.14 g of desired 1-(4-trifluoromethoxyphenyl)-1,4-dihydro-4-oxo-5-fluorocinnoline-3-carboxylic acid (yield: 99.5%). m.p., 200° C. (decomposed)

Workup

  1. washwashed with diethyl ether (30 ml)
  2. customto precipitate crystals
  3. filtrationThe precipitated crystals was collected by filtration
  4. washwashed two times with water (20 ml)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc919835f3704103b4d4a5a7718d704b
Source dataset
uspto-grants-1989_10
Patent number
US04875924

Reaction notes

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