Ammonia → HCID 13960223, compound

HRID 2413966Notes

Reaction equation

HRID 2413966 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([F:27])=[C:19]([N:20]3[CH2:25][CH2:24][NH:23][CH:22]([CH3:26])[CH2:21]3)[C:12]3=[C:13]2[N:8]([CH:9]([CH3:29])[CH2:10][C:11]3=[O:28])[CH:7]=1)=[O:5])C.N>C(O)C.Cl>[F:27][C:18]1[CH:17]=[C:14]2[C:13]3[N:8]([CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15]2=[O:16])[CH:9]([CH3:29])[CH2:10][C:11](=[O:28])[C:12]=3[C:19]=1[N:20]1[CH2:25][CH2:24][NH:23][CH:22]([CH3:26])[CH2:21]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 54525278HCID 54525278, compound

Product 1

HCID 13960223HCID 13960223, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

4.01 g (0.01 mole) of 9-fluoro-5-methyl-8-(3-methyl-1-piperazinyl)-6,7-dihydro-1, 7-dioxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester was suspended in a mixture of 20 ml of ethanol and 20 ml of 6N hydrochloric acid, and this suspension was stirred at 80°-90° C. for 5 hours to hydrolyze the starting material. The resulting reaction solution was adjusted to pH 7-8 by the addition of 28% aqueous ammonia under cooling with ice. The precipitate which separated out was collected by filtration and recrystallized from a water-ethanol mixture (with a volume ratio of 1:1) to obtain 2.69 g (72.0% yield) of 9-fluoro-5-methyl-8-(3-methyl-1-piperazinyl)-6,7-dihydro-1, 7-dioxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid in the form of yellow crystals. These crystals had a melting point of 231°-234° C. (dec.) .

Workup

  1. customThe resulting reaction solution
  2. temperatureunder cooling with ice
  3. customThe precipitate which separated out
  4. filtrationwas collected by filtration
  5. customrecrystallized from a water-ethanol mixture (with a volume ratio of 1:1)

Sources & evidence

ORD record
ord-7feca473803042c4b2d193edf5b88d13
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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