Formaldehyde → HCID 18401802, compound

HRID 377295Notes

Reaction equation

HRID 377295 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[CH2:21][NH:20][CH2:19]5)[C:12]=3[O:14][CH3:15])[C:7](=[O:25])[C:6]([C:26]([OH:28])=[O:27])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:29]=O>C(O)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[CH2:21][N:20]([CH3:29])[CH2:19]5)[C:12]=3[O:14][CH3:15])[C:7](=[O:25])[C:6]([C:26]([OH:28])=[O:27])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 502078HCID 502078, compound

Product 1

HCID 18401802HCID 18401802, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To 100 mg of 1-cyclopropyl-7-(isoindolin-5-yl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid were added 1 ml of formic acid and 65 mg of formalin, and the resulting mixture was heated under reflux for 1 hour, after which the solvent was distilled under reduced pressure to remove the solvent. To the resulting residue was added 5 ml of water, and the resulting mixture was adjusted to pH 7 with a saturated aqueous sodium hydrogencarbonate solution and extracted with five 5-ml portions of chloroform. The chloroform layer obtained was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. To the resulting residue were added ethanol and diethyl ether, and the crystals were collected by filtration. To the crystals collected were added 1 ml of ethanol, 1 ml of a 1N aqueous sodium hydroxide solution and 1 ml of water to dissolve the crystals, after which carbon dioxide was bubbled into the resulting solution and the crystals were collected by filtration to obtain 76 mg of light-yellow 1-cyclopropyl-8-methoxy-7-(2-methylisoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. distillationafter which the solvent was distilled under reduced pressure
  4. customto remove the solvent
  5. additionTo the resulting residue was added 5 ml of water
  6. extractionextracted with five 5-ml portions of chloroform
  7. customThe chloroform layer obtained
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. additionTo the resulting residue were added ethanol and diethyl ether
  12. filtrationthe crystals were collected by filtration
  13. customTo the crystals collected
  14. additionwere added 1 ml of ethanol, 1 ml of a 1N aqueous sodium hydroxide solution and 1 ml of water
  15. dissolutionto dissolve the crystals
  16. customafter which carbon dioxide was bubbled into the resulting solution
  17. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-b29dc511008b4da5abd854fb022e6fea
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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