3-Hydroxypiperidine → 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-hydroxy-1-piperidinyl)-4-oxoquinoline-3-carboxylic acid

HRID 434569Notes

Reaction equation

HRID 434569 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[OH:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:23]3[CH2:24][CH2:25][CH2:26][CH:21]([OH:20])[CH2:22]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 232933-HydroxypiperidineHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 127709151-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-hydroxy-1-piperidinyl)-4-oxoquinoline-3-carboxylic acidYield 53.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (0.43 g), 3-hydroxypiperidine (1.6 g), and pyridine (3 ml) was refluxed for 6 hours. The mixture was evaporated to dryness, treated with water, acidified with acetic acid, and extracted with dichloromethane. The dichloromethane layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was recrystallized from a mixture of DMF and ethanol to give 1-ethyl-6,8-difluoro-1,4-dihydro-7-(3-hydroxy-1-piperidinyl)-4-oxoquinoline-3-carboxylic acid (0.3 g), mp 232°-234° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe mixture was evaporated to dryness
  3. additiontreated with water
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe residue was recrystallized from a mixture of DMF and ethanol

Sources & evidence

ORD record
ord-237c93292e9446819bded5bdef3be032
Source dataset
uspto-grants-1983_08
Patent number
US04398029

Reaction notes

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