HCID 19841134, compound → HCID 19841155, compound

HRID 1638691Notes

Reaction equation

HRID 1638691 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:29])=[C:11]([N:16]4[CH2:21][CH2:20][N:19](CC5C=CC=CC=5)[CH2:18][CH2:17]4)[C:12]=3[CH2:14][OH:15])[C:7](=[O:30])[C:6]([C:31]([OH:33])=[O:32])=[CH:5]2)[CH2:3][CH2:2]1>[Pd].C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:29])=[C:11]([N:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]4)[C:12]=3[CH2:14][OH:15])[C:7](=[O:30])[C:6]([C:31]([OH:33])=[O:32])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 19841134HCID 19841134, compound

Product 1

HCID 19841155HCID 19841155, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 1-cyclopropyl-7-(4-benzyl-1-piperazinyl)-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (132 mg) are added 10% Pd-C (68 mg) and ethanol (10 ml), and the mixture is subjected to catalytic reduction under hydrogen gas atmosphere at 60° C. for 6.5 hours. After filtering off the catalyst, the filtrate is concentrated. The resulting residue is recrystallized from ethanol-acetone-dichloromethane to give 1-cyclopropyl-7-(1-piperazinyl)-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (34.2 mg), as white powder, m.p. 149°-152° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate is concentrated
  3. customThe resulting residue is recrystallized from ethanol-acetone-dichloromethane

Sources & evidence

ORD record
ord-22529f3fa8c94bb1a26bdb83a1d74f71
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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