Hydrochloric Acid → 2-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

HRID 894167Notes

Reaction equation

HRID 894167 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[C:4]=2[CH:3]=1.Cl.[CH3:19][N:20](C)C=O>>[C:19]([C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[C:4]=2[CH:3]=1)#[N:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 129291312-Bromo-6H-dibenz[b,e]oxepin-11-one

Product 1

HCID 124468252-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

Conditions

Temperature
100 °C

Procedure

Reflux 43 gm. (0.1488 mole of 2-bromo-6,11-dihydro-11-oxodibenz[b,e]oxepin and 16 gm. (0.178 mole, 20% excess) of cuprous cyanide in 150 cc. of N,N-dimethylformamide for 24 hours. Cool to 100° C. and pour into a solution of 100 gm. of ferric chloride in 140 cc. of 5% aqueous hydrochloric acid with stirring. Keep the mixture at 70° C. for 30 minutes cool, filter and wash the solids with water. Dissolve the solids in methylene chloride and purify by filtering through a short column of silica gel (m.p. 160°-161° C.).

Workup

  1. temperatureReflux 43 gm
  2. additionpour into a solution of 100 gm
  3. customat 70° C.
  4. customfor 30 minutes
  5. temperaturecool
  6. filtrationfilter
  7. washwash the solids with water
  8. dissolutionDissolve the solids in methylene chloride
  9. custompurify
  10. filtrationby filtering through a short column of silica gel (m.p. 160°-161° C.)

Sources & evidence

ORD record
ord-46c4d7901bb44dac8a6732810125ea9b
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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