Ethyl 9-[3-(3,4-dimethylphenyl)piperazin-1-yl]-8-fluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f] [1,7]naphthyridine-2-carboxylate → 9-[3-(3,4-Dimethylphenyl)piperazin-1-yl]-8-fluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acid

HRID 413058Notes

Reaction equation

HRID 413058 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:14][CH2:13][CH2:12][N:11]([C:15]3[C:16]([F:36])=[CH:17][C:18]4[N:27]=[CH:26][C:25]5[N:24]([CH3:28])[CH:23]=[C:22]([C:29]([O:31]CC)=[O:30])[C:21](=[O:34])[C:20]=5[C:19]=4[CH:35]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]>C(O)C.[OH-].[K+].O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:14][CH2:13][CH2:12][N:11]([C:15]3[C:16]([F:36])=[CH:17][C:18]4[N:27]=[CH:26][C:25]5[N:24]([CH3:28])[CH:23]=[C:22]([C:29]([OH:31])=[O:30])[C:21](=[O:34])[C:20]=5[C:19]=4[CH:35]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 1

HCID 18523411Ethyl 9-[3-(3,4-dimethylphenyl)piperazin-1-yl]-8-fluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f] [1,7]naphthyridine-2-carboxylate

Product 1

HCID 185232699-[3-(3,4-Dimethylphenyl)piperazin-1-yl]-8-fluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acidYield 70.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred suspension of 1.47 g of ethyl 9-[3-(3,4-dimethylphenyl)piperazin-1-yl]-8-fluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate in 25 cm3 of ethanol, 3.60 cm3 of 1 N aqueous potassium hydroxide and 15 cm3 of water was heated in the region of 100° C. for 4 hours. The reaction mixture was filtered, evaporated to dryness, the residue was suspended in 100 cm3 of water, the medium was acidified with 3.5 cm3 of a 1 N aqueous hydrochloric acid solution, 10 cm3 of ethanol was added, the medium was heated to 100° C. and filtered at high temperature. The residue was washed 3 times with 25 cm3 of water and then with 10 cm3 of ethanol. 0.98 g of 9-[3-(3,4-dimethylphenyl)piperazin-1-yl]-8-fluoro-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 325° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. additionwas added
  4. temperaturethe medium was heated to 100° C.
  5. filtrationfiltered at high temperature
  6. washThe residue was washed 3 times with 25 cm3 of water

Sources & evidence

ORD record
ord-83035f8a2f7748c193764943a6adadf3
Source dataset
uspto-grants-2003_05
Patent number
US06566362B2

Reaction notes

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