Acetic Acid → 8-Fluoro-2-methyl-9-(4-methyl-1-piperazinyl)-7-amino-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

HRID 1981899Notes

Reaction equation

HRID 1981899 reaction equation
[F:1][C:2]1[C:3]([NH2:20])=[C:4]2[C:9]3=[C:10]([CH2:13][CH:14]([CH3:15])[N:8]3[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19])[C:11]=1F.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[OH-].[Na+].C(O)(=O)C>CN1CCCC1=O.O>[F:1][C:2]1[C:3]([NH2:20])=[C:4]2[C:9]3=[C:10]([CH2:13][CH:14]([CH3:15])[N:8]3[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19])[C:11]=1[N:25]1[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 133771777-Amino-8,9-difluoro-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

Product 1

HCID 133771788-Fluoro-2-methyl-9-(4-methyl-1-piperazinyl)-7-amino-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

8,9-Difluoro-7-amino-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (2 g) and N-methylpiperazine (4 ml) are suspended in N-methylpyrrolidone (20 ml), and the mixture is heated at 110°-120° C. on an oil bath for 3 hours. After the reaction, the reaction mixture is distilled under reduced pressure, and to the residue is added ethyl acetate. The resulting crystals are separated by filtration and thereto is added water (80 ml), which is regulated to pH 2 with 6N hydrochloric acid, and the mixture is heated at 50° C. and then filtered. The filtrate is concentrated to dryness, and the residue is recrystallized from ethanol-water to give yellow cubic crystals. The crystals are again suspended in water (10 ml) and is dissolved by regulating to pH 12 with a 10% aqueous sodium hydroxide solution and then is regulated to pH 8 with acetic acid. The precipitated crystals are separated by filtration, washed with water and dried to give 8-fluoro-2-methyl-9-(4-methyl-1-piperazinyl)-7-amino-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline- 5-carboxylic acid (1.4 g) as yellow cubic crystals. m.p. 240°-243° C.

Workup

  1. temperaturethe mixture is heated at 110°-120° C. on an oil bath for 3 hours
  2. customAfter the reaction
  3. distillationthe reaction mixture is distilled under reduced pressure
  4. additionto the residue is added ethyl acetate
  5. customThe resulting crystals are separated by filtration
  6. additionis added water (80 ml), which
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated to dryness
  9. customthe residue is recrystallized from ethanol-water
  10. customto give yellow cubic crystals
  11. dissolutionis dissolved
  12. customThe precipitated crystals are separated by filtration
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-7001e66b8316440c83372eb68c3c8f64
Source dataset
uspto-grants-1986_06
Patent number
US04594347

Reaction notes

Loading…