Acetic Acid → Oxcarbazepine

HRID 1380000Notes

Reaction equation

HRID 1380000 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 (=0.11 mole) are added to a suspension of 26.3 g (0.1 mole) of 5-cyano-10-nitro-5H-dibenz[b,f]azepine in 100 ml of acetic acid at room temperature. In the course of this the temperature rises slowly to 34° with complete dissolution of the starting material. 30 ml of water are added at 30° in the course of 5 minutes, resulting in a further increase in temperature to 37°. At this temperature 40 g of iron powder are added in portions over a period of 20 minutes, the temperature being maintained at 65°-70° by occasional cooling. After the exothermic reaction has subsided, stirring is continued for a further 15 minutes and then inorganic material is filtered off and washed three times with a little acetic acid. The total filtrate is added dropwise, while stirring well, to 11/2 l of water and, after stirring for 2 hours, the resulting precipitate is filtered off and washed neutral with water. After drying in vacuo at 60°, 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. dissolutionIn the course of this the temperature rises slowly to 34° with complete dissolution of the starting material
  2. customresulting in
  3. temperaturea further increase in temperature to 37°
  4. temperaturethe temperature being maintained at 65°-70° by occasional cooling
  5. customAfter the exothermic reaction
  6. filtrationinorganic material is filtered off
  7. washwashed three times with a little acetic acid
  8. additionThe total filtrate is added dropwise
  9. stirringwhile stirring well, to 11/2 l of water
  10. stirringafter stirring for 2 hours
  11. filtrationthe resulting precipitate is filtered off
  12. washwashed neutral with water
  13. customAfter drying in vacuo at 60°

Sources & evidence

ORD record
ord-be6de81fe71a44ee8f5f004939279e14
Source dataset
uspto-grants-1986_04
Patent number
US04579683

Reaction notes

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