Potassium Hydroxide → HCID 18523413, compound

HRID 413055Notes

Reaction equation

HRID 413055 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:24]=[CH:23][C:7]2[C:8]3[C:9](=[O:22])[C:10]([C:17]([O:19]CC)=[O:18])=[CH:11][N:12]([CH3:16])[C:13]=3[CH:14]=[N:15][C:6]=2[C:5]=1[N:25]1[CH2:30][CH2:29][C:28]([OH:41])([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[CH2:27][CH2:26]1>C(O)C.O>[F:3][C:4]1[CH:24]=[CH:23][C:7]2[C:8]3[C:9](=[O:22])[C:10]([C:17]([OH:19])=[O:18])=[CH:11][N:12]([CH3:16])[C:13]=3[CH:14]=[N:15][C:6]=2[C:5]=1[N:25]1[CH2:30][CH2:29][C:28]([OH:41])([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18523244HCID 18523244, compound

Product 1

HCID 18523413HCID 18523413, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1.02 cm3 of 1 N aqueous potassium hydroxide was added, with stirring, to a suspension of 0.46 g of ethyl 8-fluoro-7-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidin-1-yl]-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate in 5 cm3 of ethanol and 4 cm3 of water. The mixture was heated at about 80° C. for 2 hours and then evaporated to dryness. The residue was dissolved in 20 cm3 of water, the aqueous phase was washed with 20 cm3 of dichloromethane, acidified with 0.06 cm3 of acetic acid and then extracted 3 times with 50 cm3 of dichloromethane. The organic phase was dried over magnesium sulphate and concentrated to dryness under reduced pressure (20 kPa). The residue obtained was washed twice with 5 cm3 of diisopropyl ether and dried. 0.22 g of 8-fluoro-7-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidin-1-yl]-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acid was obtained in the form of a yellow solid, which melted at 245° C.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in 20 cm3 of water
  3. washthe aqueous phase was washed with 20 cm3 of dichloromethane
  4. extractionextracted 3 times with 50 cm3 of dichloromethane
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (20 kPa)
  7. customThe residue obtained
  8. washwas washed twice with 5 cm3 of diisopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-da89e22250ec4e42a5e9f798779af560
Source dataset
uspto-grants-2003_05
Patent number
US06566362B2

Reaction notes

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