Acetic Acid → Oxcarbazepine

HRID 1380002Notes

Reaction equation

HRID 1380002 reaction equation
B(F)(F)F.[C:5]([N:7]1[C:13]2C=[CH:15][CH:16]=[CH:17][C:12]=2C([N+]([O-])=O)=[CH:10][C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]1=2)#[N:6].[OH2:25].[C:26]([OH:29])(=O)[CH3:27]>[Fe]>[C:5]([N:7]1[C:13]2[CH:12]=[CH:17][CH:16]=[CH:15][C:27]=2[C:26](=[O:29])[CH2:10][C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]1=2)(=[O:25])[NH2:6]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 962WaterHCID 6356Boron trifluorideHCID 2246789110-Nitro-5H-dibenz(b,f)azepine-5-carbonitrile

Product 1

HCID 34312Oxcarbazepine

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

50 ml of a solution of 15% by weight of BF3 in acetic acid are allowed to flow rapidly into a suspension of 26.3 g (0.1 mole) of 5-cyano-10-nitro-5H-dibenz[b,f]azepine in 200 ml of acetic acid. The mixture is stirred for 45 minutes until complete dissolution occurs and the moderately exothermic reaction has subsided. At 30° 40 g of iron powder are then added and 100 ml of water are slowly added dropwise in the course of 30 minutes, the temperature rising to 65°. The reaction mixture is stirred for 15 hours at room temperature, is heated again to 60°, and the undissolved parts are filtered off and washed three times with acetic acid. The filtrate is concentrated by evaporation in vacuo to a volume of approximately 100 ml and 400 ml of water are added dropwise. The mixture is stirred for a further 2 hours, filtered and the filter cake is washed neutral with water. After drying at 50° in vacuo, 23.8 g (94.4% of the theoretical yield) of crude product are obtained and this is recrystallised from 200 ml of acetic acid/water (8:2). Pure 5-carbamoyl-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine is obtained, which according to the IR spectrum is identical to authentic material.

Workup

  1. customthe moderately exothermic reaction
  2. customrising to 65°
  3. stirringThe reaction mixture is stirred for 15 hours at room temperature
  4. temperatureis heated again to 60°
  5. filtrationthe undissolved parts are filtered off
  6. washwashed three times with acetic acid
  7. concentrationThe filtrate is concentrated by evaporation in vacuo to a volume of approximately 100 ml and 400 ml of water
  8. additionare added dropwise
  9. stirringThe mixture is stirred for a further 2 hours
  10. filtrationfiltered
  11. washthe filter cake is washed neutral with water
  12. customAfter drying at 50° in vacuo, 23.8 g (94.4% of the
  13. customtheoretical yield) of crude product
  14. customare obtained
  15. customthis is recrystallised from 200 ml of acetic acid/water (8:2)

Sources & evidence

ORD record
ord-17541d834b55426c88d0cb2b19daf4df
Source dataset
uspto-grants-1986_04
Patent number
US04579683

Reaction notes

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