Acetic Acid → (RS)-7,9-difluoro-1-methyl-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 1084406Notes

Reaction equation

HRID 1084406 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:30])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:22]4[CH2:27][CH2:26][NH:25][CH:24]([CH3:28])[CH2:23]4)=[C:17]([F:29])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])C.[OH-].[K+].C(O)(=O)C>C(O)C>[F:21][C:19]1[C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH:24]([CH3:28])[CH2:23]2)=[C:17]([F:29])[C:11]2=[N:12][C:13]3[N:14]([CH3:16])[CH:15]=[C:6]([C:4]([OH:5])=[O:3])[C:7](=[O:30])[C:8]=3[CH:9]=[C:10]2[CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 20063299(RS)-3-ethoxycarbonyl-7,9-difluoro-1-methyl-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine

Product 1

HCID 20063294(RS)-7,9-difluoro-1-methyl-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acidYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1.5 g of (RS)-3-ethoxycarbonyl-7,9-difluoro-1-methyl-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine in 20 cm3 of ethanol and 20 cm3 of N aqueous potassium hydroxide solution is heated at a temperature close to 75° C. for 1 hour and a half. 12 g of a 10% aqueous solution of acetic acid is added to the solution obtained, at this latter temperature. The insoluble matter obtained is drained at about 75° C. and washed 3 times with 30 cm3 of water at about 20° C. After recrystallizing once from 100 cm3 of dimethylformamdide, 0.9 g of (RS)-7,9-difluoro-1-methyl-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a yellow solid melting at 380°-382° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 75° C. for 1 hour
  3. customobtained, at this latter temperature
  4. customThe insoluble matter obtained
  5. customis drained at about 75° C.
  6. washwashed 3 times with 30 cm3 of water at about 20° C
  7. customAfter recrystallizing once from 100 cm3 of dimethylformamdide

Sources & evidence

ORD record
ord-e6149e04f47e47ef8138b371626d65c4
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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