Water → 10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carbonitrile

HRID 1934786Notes

Reaction equation

HRID 1934786 reaction equation
[C:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2].BrN1C(=[O:24])CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>ClC1C=CC=CC=1>[C:1]([N:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH:6]([OH:24])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 1116033810,11-Dihydro-5H-dibenzo[b,f]azepine-5-carbonitrile

Product 1

HCID 994277310,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carbonitrileYield 52%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

6.60 g (0.030 mols) of (I) are dissolved in 45 ml of chlorobenzene, the mixture is heated to 50° C. under stirring. The resulting solution is added under stirring with 5.6 g (0.0315 mols) of N-bromosuccinimide then with 0.49 g (0.003 mols) of azobisisobutyronitrile, stirring for 1 hour while heating at 75-80° C. The mixture is then is cooled to 40° C., added with 30 ml of water and stirred at 40° C. for 30 minutes, then heated to 80° C. for 3 hours. After decanting for 30 minutes, the aqueous phase is separated and re-extracted with 8 ml of chlorobenzene. The combined organic phases are washed with water (10 ml) and dried, then concentrated at 60° C. to 20 ml, adding 15 ml of hexane at this temperature. The mixture is cooled to 0-5° C. for 30 minutes and the separated solid is filtered, to obtain 3.68 g (52%) of 5-cyano-10-hydroxy-10,11-dihydro-5H-dibenz[b,f]azepine (VI), m.p. 117-8° C., purity>98% (HPLC).

Workup

  1. additionThe resulting solution is added
  2. temperaturewhile heating at 75-80° C
  3. temperatureThe mixture is then is cooled to 40° C.
  4. stirringstirred at 40° C. for 30 minutes
  5. temperatureheated to 80° C. for 3 hours
  6. customAfter decanting for 30 minutes
  7. customthe aqueous phase is separated
  8. extractionre-extracted with 8 ml of chlorobenzene
  9. washThe combined organic phases are washed with water (10 ml)
  10. customdried
  11. concentrationconcentrated at 60° C. to 20 ml
  12. additionadding 15 ml of hexane at this temperature
  13. temperatureThe mixture is cooled to 0-5° C. for 30 minutes
  14. filtrationthe separated solid is filtered

Sources & evidence

ORD record
ord-2972b88aac63439a85da059a99742f96
Source dataset
uspto-grants-2002_05
Patent number
US06384217B1

Reaction notes

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