Formaldehyde → (+)-1-Ethyl-6,8-difluoro-7-[3-(fluoromethyl)-4-methyl-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2165689Notes

Reaction equation

HRID 2165689 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:22])=[C:10]([N:14]3[CH2:19][CH2:18][NH:17][CH:16]([CH2:20][F:21])[CH2:15]3)[C:11]=2[F:13])[C:6](=[O:23])[C:5]([C:24]([OH:26])=[O:25])=[CH:4]1)[CH3:2].[C:27]([O-])(=O)C.[Na+].C=O>C(O)=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:22])=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([CH3:27])[CH:16]([CH2:20][F:21])[CH2:15]3)[C:11]=2[F:13])[C:6](=[O:23])[C:5]([C:24]([OH:26])=[O:25])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 14839398(+)-1-Ethyl-6,8-difluoro-7-[3-(fluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 14839399(+)-1-Ethyl-6,8-difluoro-7-[3-(fluoromethyl)-4-methyl-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 70.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 150 mg of (-)-1-ethyl-6,8-difluoro-7-[3-(fluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Ex. 64) was reacted as described previously with 400 mg of sodium acetate, 3 ml of formic acid and 3 ml of formaldehyde, giving 110 mg of the desired product, mp 208°-210° C. (dec.).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-1274e175a5c8416b8b8a3d24a01be728
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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