Hydrochloric Acid → 9-Fluoro-4-methyl-1-oxo-8-pyrrolidinyl-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acid

HRID 413062Notes

Reaction equation

HRID 413062 reaction equation
[F:1][C:2]1[C:3]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:4][C:5]2[N:14]=[CH:13][C:12]3[N:11]([CH3:15])[CH:10]=[C:9]([C:16]([O:18]CC)=[O:17])[C:8](=[O:21])[C:7]=3[C:6]=2[CH:22]=1.[OH-].[K+].Cl>C(O)C>[F:1][C:2]1[C:3]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:4][C:5]2[N:14]=[CH:13][C:12]3[N:11]([CH3:15])[CH:10]=[C:9]([C:16]([OH:18])=[O:17])[C:8](=[O:21])[C:7]=3[C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18523362Ethyl 9-fluoro-4-methyl-1-oxo-8-pyrrolidinyl-1,4-dihydrobenzo[f] [1,7]naphthyridine-2-carboxylate

Product 1

HCID 185232609-Fluoro-4-methyl-1-oxo-8-pyrrolidinyl-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 0.8 g of ethyl 9-fluoro-4-methyl-1-oxo-8-pyrrolidinyl-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate in a mixture of 60 Cm3 of aqueous ethanol at 50% and 2.8 cm3 of a 1 N aqueous potassium hydroxide solution was heated, with stirring, for 2 hours at a temperature of 70° C. After concentration under reduced pressure (5.2 kPa) at 60° C., the residue was dissolved in 100 cm3 of water; the light insoluble material was removed by filtration. The solution obtained was neutralized with 2.8 cm3 of a 1 N aqueous hydrochloric acid solution. The insoluble material formed was dewatered, washed 3 times with 20 cm of water, twice with 15 cm3 of ethanol and dried under vacuum at 100° C. 0.65 g of 9-fluoro-4-methyl-1-oxo-8-pyrrolidinyl-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acid was obtained in the form of yellow crystals, which melted at 365° C.

Workup

  1. temperaturewas heated
  2. concentrationAfter concentration under reduced pressure (5.2 kPa) at 60° C.
  3. dissolutionthe residue was dissolved in 100 cm3 of water
  4. customthe light insoluble material was removed by filtration
  5. customThe solution obtained
  6. customThe insoluble material formed
  7. washwashed 3 times with 20 cm of water
  8. dry with materialtwice with 15 cm3 of ethanol and dried under vacuum at 100° C

Sources & evidence

ORD record
ord-f540022aa6204cf1898db23e4fed415d
Source dataset
uspto-grants-2003_05
Patent number
US06566362B2

Reaction notes

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