2-Pyrrolidone → HCID 13191949, compound

HRID 434693Notes

Reaction equation

HRID 434693 reaction equation
Cl[C:2]1[C:11]2[CH2:12][CH:13]([CH3:14])[N:9]3[C:10]=2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]3)=[CH:4][C:3]=1[F:19].[NH:20]1[CH2:24][CH2:23][CH2:22][C:21]1=O>CN(C)P(=O)(N(C)C)N(C)C>[N:20]1([C:2]2[C:11]3[CH2:12][CH:13]([CH3:14])[N:9]4[C:10]=3[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]4)=[CH:4][C:3]=2[F:19])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 120252-PyrrolidoneHCID 13135548HCID 13135548, compound

Product 1

HCID 13191949HCID 13191949, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

A mixture of 56 g of 9-chloro-8-fluoro-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid, 71 g of pyrrolidone and 60 ml of hexamethylphosphoric triamide in a stainless steel autoclave was reacted at 150° C. for 8 hours. After completion of reaction, hexamethylphosphoric triamide was distilled off under reduced pressure and the residue was recrystallized repeatedly from dimethylformamide to give 25 g of 9-(1-pyrrolidinyl)-8-fluoro-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid. m.p. not lower than 300° C., pale yellow rhombic crystals.

Workup

  1. customwas reacted at 150° C. for 8 hours
  2. distillationwas distilled off under reduced pressure
  3. customthe residue was recrystallized repeatedly from dimethylformamide

Sources & evidence

ORD record
ord-8828d21d6db64a65995c8db756b60f40
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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