Methyl iodide → 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 1981904Notes

Reaction equation

HRID 1981904 reaction equation
[N:1]1([C:7]2[C:16]3[CH2:17][CH:18]([CH3:19])[N:14]4[C:15]=3[C:10]([C:11](=[O:23])[C:12]([C:20]([OH:22])=[O:21])=[CH:13]4)=[C:9]([NH2:24])[C:8]=2[F:25])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:27](I)(F)F.CI>CN(C)C=O>[CH3:27][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:16]3[CH2:17][CH:18]([CH3:19])[N:14]4[C:15]=3[C:10]([C:11](=[O:23])[C:12]([C:20]([OH:22])=[O:21])=[CH:13]4)=[C:9]([NH2:24])[C:8]=2[F:25])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 16843TrifluoroiodomethaneHCID 13377179HCID 13377179, compound

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 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of 9-(1-piperazinyl)-8-fluoro-7-amino-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (3.45 g) and dimethylformamide (20 ml) is added a dimethylformamide solution (20 ml) of trifluoromethyl iodide containing methyl iodide (7.7 g), and the mixture is reacted in a stainless steel autoclave on an oil bath at 110°-120° C. for 5 hours. After completion of reaction, dimethylformamide is distilled off under reduced pressure, and to the residue is added a 10% aqueous sodium hydroxide solution. Insoluble materials are removed by filtration. The filtrate is regulated to pH 8 with acetic acid, and the precipitated crystal is separated by filtration, washed with water, and dried to give 9-(4-methyl-1-piperazinyl)-8-fluoro-7-amino-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (1.82 g) as yellow cubic crystals. m.p. 240°-243° C.

Workup

  1. distillationis distilled off under reduced pressure
  2. additionto the residue is added a 10% aqueous sodium hydroxide solution
  3. customInsoluble materials are removed by filtration
  4. customthe precipitated crystal is separated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-714474358c00410f8a27baa26c7ce674
Source dataset
uspto-grants-1986_06
Patent number
US04594347

Reaction notes

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