Formaldehyde → 7-[3-(5-Bromo-2-thienyl)-4-methyl-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2165613Notes

Reaction equation

HRID 2165613 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]3[CH:22]=[C:21]4[C:16]([C:17](=[O:28])[C:18]([C:25]([OH:27])=[O:26])=[CH:19][N:20]4[CH2:23][CH3:24])=[CH:15][C:14]=3[F:29])[CH2:8]2)=[CH:4][CH:3]=1.[CH2:30]=O>C(O)(=O)C>[Br:1][C:2]1[S:6][C:5]([CH:7]2[N:12]([CH3:30])[CH2:11][CH2:10][N:9]([C:13]3[CH:22]=[C:21]4[C:16]([C:17](=[O:28])[C:18]([C:25]([OH:27])=[O:26])=[CH:19][N:20]4[CH2:23][CH3:24])=[CH:15][C:14]=3[F:29])[CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 148393577-[3-(5-Bromo-2-thienyl)-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 148393587-[3-(5-Bromo-2-thienyl)-4-methyl-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 150 mg portion of 7-[3-(5-bromo-2-thienyl)-1piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was dissolved in a mixture of 0.6 ml of 37% formaldehyde and 0.75 ml of glacial acetic acid, heated on a steam bath for 2 hours and then evaporated. The residue was diluted with 3 ml of water, adjusted to pH 7 with 1N sodium hydroxide and the solid collected, giving 120 mg of the desired product, mp 243°-245° C. (dec.).

Workup

  1. temperatureheated on a steam bath for 2 hours
  2. customevaporated
  3. additionThe residue was diluted with 3 ml of water
  4. customthe solid collected

Sources & evidence

ORD record
ord-395b0dd31a2a454bb8204d37c5c64331
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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