3-Hydroxypiperidine → 8-Fluoro-9-(3-hydroxy-1-piperidyl)-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

HRID 434696Notes

Reaction equation

HRID 434696 reaction equation
[F:1][C:2]1[CH:3]=[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.[OH:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1>CN(C)P(=O)(N(C)C)N(C)C>[F:1][C:2]1[CH:3]=[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:23]1[CH2:24][CH2:25][CH2:26][CH:21]([OH:20])[CH2:22]1

Participants

4

Reactant 2

HCID 232933-Hydroxypiperidine2×HCID 131355588,9-Difluoro-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

Product 1

HCID 131919568-Fluoro-9-(3-hydroxy-1-piperidyl)-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acidYield 38.3%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

8,9-Difluoro-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (5 g) and a solution of 7.5 g of 3-hydroxypiperidine in 50 ml of hexamethylphosphoric triamide were reacted with heating at 120° to 130° C. for 7 hours with stirring. After completion of reaction, hexamethylphosphoric triamide and unreacted 3-hydroxypiperidine were distilled off under reduced pressure. Recrystallization of the residue from dimethylformamide gave 2.5 g of 8-fluoro-9-(3-hydroxy-1-piperidyl)-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid. m.p. 251°-253° C.

Workup

  1. temperaturewith heating at 120° to 130° C. for 7 hours
  2. distillationwere distilled off under reduced pressure
  3. customRecrystallization of the residue from dimethylformamide

Sources & evidence

ORD record
ord-aaa641dc4f254d1791665aafbee775d3
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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