Formaldehyde → HCID 21220222, compound

HRID 1584836Notes

Reaction equation

HRID 1584836 reaction equation
Br.[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:24])=[C:12]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[CH2:20][NH:19][CH2:18]5)[CH:13]=3)[C:8](=[O:25])[C:7]([C:26]([OH:28])=[O:27])=[CH:6]2)[CH2:4][CH2:3]1.C=O.O.[C:32](=O)([O-])O.[Na+]>C(O)=O>[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:24])=[C:12]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[CH2:20][N:19]([CH3:32])[CH2:18]5)[CH:13]=3)[C:8](=[O:25])[C:7]([C:26]([OH:28])=[O:27])=[CH:6]2)[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 516892Sodium BicarbonateHCID 69960490HCID 69960490, compound

Product 1

HCID 21220222HCID 21220222, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In 0.50 ml of formic acid was suspended 50 mg of 1-cyclopropyl-6-fluoro-7-(isoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrobromide, and 27 mg of formalin was added to the suspension, after which the mixture was heated under reflux for two hours. The solvent was then removed by distillation under reduced pressure. To the residue obtained was added 5 ml of water and the pH was adjusted to 7 with a saturated aqueous sodium hydrogencarbonate solution, after which the resulting mixture was extracted with five 5 ml portions of chloroform. The resulting chloroform layer was dried over anhydrous magnesium sulfate and then the solvent was removed by distillation under reduced pressure. Ethanol was added to the residue obtained and the crystals formed were collected by filtration, to obtain 29 mg of pale yellow, crystalline 1-cyclopropyl-6-fluoro-7-(2-methylisoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. additionwas added to the suspension
  2. temperatureafter which the mixture was heated
  3. temperatureunder reflux for two hours
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customTo the residue obtained
  6. extractionafter which the resulting mixture was extracted with five 5 ml portions of chloroform
  7. dry with materialThe resulting chloroform layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. additionEthanol was added to the residue
  10. customobtained
  11. customthe crystals formed
  12. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-31ee2d66611e4427b03c8def7554e720
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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