10-Methoxyiminostilbene → DE(5-carboxamide)oxcarbazepine

HRID 2393731Notes

Reaction equation

HRID 2393731 reaction equation
C[O:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1>Cl>[O:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH2:4]1

Participants

3

Reactant 1

HCID 7842410-Methoxyiminostilbene

Product 1

HCID 11160106DE(5-carboxamide)oxcarbazepine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

22.3 g of 10-methoxy-5H-dibenz(b,f)azepine are heated under reflux with 100 ml of 2N hydrochloric acid for 2 hours. The gummy residue is extracted with chloroform (50÷50 ml), the combined extracts are washed with water and evaporated to dryness under vacuum. The residue is taken up into 200 ml of ethanol, treated with charcoal (2 g) for 1 h under reflux, filtered, evaporated to dryness under vacuum, finally taken up into 50÷50 ml of toluene, stripping thoroughly. The residue is kept for further working-up.

Workup

  1. extractionThe gummy residue is extracted with chloroform (50÷50 ml)
  2. washthe combined extracts are washed with water
  3. customevaporated to dryness under vacuum
  4. additiontreated with charcoal (2 g) for 1 h
  5. temperatureunder reflux
  6. filtrationfiltered
  7. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-9f518891f9d3470ca3e74e568cdebc92
Source dataset
uspto-grants-1998_09
Patent number
US05808058

Reaction notes

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