Formaldehyde → HCID 20133480, compound

HRID 845030Notes

Reaction equation

HRID 845030 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:18])[C:11]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[N:8]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH:7]=[C:6]([C:26]([OH:28])=[O:27])[C:5]2=[O:29].[CH2:30]=O>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:18])[C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:30])[CH2:14][CH2:13]1)[N:8]([C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[CH:7]=[C:6]([C:26]([OH:28])=[O:27])[C:5]2=[O:29]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21290575HCID 21290575, compound

Product 1

HCID 20133480HCID 20133480, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

6,8-Difluoro-1-(4-hydroxyphenyl)-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.80 g) is added slowly to a mixture of 90% formic acid (4 ml) and 37% formaline (4 ml) under ice-cooling. After the addition, the mixture is refluxed for 5 hours. The reaction mixture is distilled to dryness under reduced pressure. The residue is suspended in saturated aqueous sodium hydrogen carbonate (15 ml), and the mixture is stirred at room temperature for 30 minutes. The precipitated crystals are separated by filtration, washed with water, dried, and then recrystallized from DMF to give 6,8-difluoro-1-(4-hydroxyphenyl)-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.52 g) as pale yellowish white crystals, m.p. 300° C.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. temperaturethe mixture is refluxed for 5 hours
  4. distillationThe reaction mixture is distilled to dryness under reduced pressure
  5. customThe precipitated crystals are separated by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from DMF

Sources & evidence

ORD record
ord-1d6740fd309f4eb690ff3a10e20fbf20
Source dataset
uspto-grants-1988_07
Patent number
US04755513

Reaction notes

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