Formaldehyde → 1-Ethyl-6-fluoro-1,4-dihydro-7-[4-methyl-3-(phenoxy-methyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

HRID 2165611Notes

Reaction equation

HRID 2165611 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:27])=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH:15]([CH2:19][O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:14]3)[CH:11]=2)[C:6](=[O:28])[C:5]([C:29]([OH:31])=[O:30])=[CH:4]1)[CH3:2].[CH2:32]=O>C(O)=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:27])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:32])[CH:15]([CH2:19][O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:14]3)[CH:11]=2)[C:6](=[O:28])[C:5]([C:29]([OH:31])=[O:30])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 148393551-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(phenoxymethyl)-1-piperazinyl]-3-quinolinecarboxylic acid

Product 1

HCID 148393561-Ethyl-6-fluoro-1,4-dihydro-7-[4-methyl-3-(phenoxy-methyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 200 mg portion of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(phenoxymethyl)-1-piperazinyl]-3-quinolinecarboxylic acid was dissolved in a mixture of 0.6 ml of 37% formaldehyde and 0.75 ml of 90% formic acid, heated on a steam bath for 3 hours and then concentrated in vacuo. The residue was dissolved in 5 ml of water and 1N sodium hydroxide was added to pH 7. The resulting solid was collected, washed with water and dried, giving 188 mg of the desired product, mp 202°-204° C.

Workup

  1. temperatureheated on a steam bath for 3 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 5 ml of water
  4. addition1N sodium hydroxide was added to pH 7
  5. customThe resulting solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-e3a6dbec47734cf8abbf49ac77c4e59c
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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