HCID 13377176, compound → 7-Amino-8,9-difluoro-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

HRID 1981898Notes

Reaction equation

HRID 1981898 reaction equation
[F:1][C:2]1[C:3]([N+:20]([O-])=O)=[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[F:12]>CN(C)C=O.[C].[Pd]>[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[F:12]

Participants

4

Reactant 1

HCID 13377176HCID 13377176, compound

Product 1

HCID 133771777-Amino-8,9-difluoro-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acidYield 49.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

8,9-Difluoro-2-methyl-7-nitro-6-oxo-1,2-dihyro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (6 g) is dissolved in dimethylformamide (300 ml) and thereto is added 20% palladium-carbon catalyst (0.5 g), and the mixture is subjected to a catalytic reduction under a pressure of 5 kg/cm2. After the reaction, the cartalyst is filtered off and further dimethylformamide is distilled off, and to the residue is added ethanol. The resulting precipited crystals are separated by filtration and recrystallized from dimethylformamide to give 8,9-difluoro-2-methyl-7-amino-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (2.7 g) as yellow cubic crystals. m.p. 270°-274° C. (decomp.)

Workup

  1. customAfter the reaction
  2. filtrationthe cartalyst is filtered off
  3. distillationfurther dimethylformamide is distilled off
  4. additionto the residue is added ethanol
  5. customThe resulting precipited crystals are separated by filtration
  6. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-0e6e26c52a1c45669a029fe50c195f80
Source dataset
uspto-grants-1986_06
Patent number
US04594347

Reaction notes

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