Formaldehyde → 1-Cyclopropyl-7-(3-methylamino-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1722305Notes

Reaction equation

HRID 1722305 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]4[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16]4)[C:12]=3[CH3:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:3][CH2:2]1.C=O.[CH:28]([O-])=O.[Na+].C(=O)([O-])O.[Na+]>C(O)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]4[CH2:19][CH2:18][CH:17]([NH:20][CH3:28])[CH2:16]4)[C:12]=3[CH3:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 2723810Sodium FormateHCID 140525771-Cyclopropyl-7-(3-amino-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 156225071-Cyclopropyl-7-(3-methylamino-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 25.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To 1-cyclopropyl-7-(3-amino-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.38 g) are added formic acid (3 ml), 37% formalin (3 ml) and sodium formate (0.4 g), and the mixture is refluxed for 5 hours. After cooling, the reaction mixture is poured into ice water and adjusted to below pH 8 with aqueous sodium hydrogen carbonate, and the mixture is extracted with dichloromethane. After removing the solvent by concentration, the resulting residue is recrystallized from ethanol-diethyl ether to give 1-cyclopropyl-7-(3-methylamino-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.1 g), as white powder, m.p. 185.5°-187.5° C. (decomp.)

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with dichloromethane
  4. customAfter removing the solvent
  5. concentrationby concentration
  6. customthe resulting residue is recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-4cfbf36499c8485d821969324e1c2b88
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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