Formaldehyde → HCID 13477661, compound

HRID 370712Notes

Reaction equation

HRID 370712 reaction equation
Cl.[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH:16]([CH3:20])[CH2:15]3)[CH:12]=2)[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]1)[CH3:3].C=O.[C:28](=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(O)=O>[CH3:20][CH:16]1[N:17]([CH3:28])[CH2:18][CH2:19][N:14]([C:11]2[CH:12]=[C:13]3[C:8]([C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5][N:4]3[CH2:2][CH3:3])=[CH:9][C:10]=2[F:21])[CH2:15]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 30624361-Ethyl-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 13477661HCID 13477661, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 2.69 g of 1-ethyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid hydrochloride, 5.4 ml 90% formic acid, 3.5 ml of 37% formalin and 0.70 g of potassium carbonate was heated for 5 hours under reflux. The reaction mixture was neutralized with 20% aqueous sodium hydroxide. The precipitate was filtered and recrystallized from a mixture of chloroform and methanol to give 1.70 g of the title compound as colorless needles, M.p. 244°-246° C.

Workup

  1. temperaturewas heated for 5 hours
  2. temperatureunder reflux
  3. filtrationThe precipitate was filtered
  4. customrecrystallized from a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-33cc7a4efff64b8caf4bf335f803e1b5
Source dataset
uspto-grants-1985_07
Patent number
US04528287

Reaction notes

Loading…