Hydrochloric Acid → 9-cyano-11H-pyrrolo[2,1-b][3]benzazepin-11-one

HRID 1438722Notes

Reaction equation

HRID 1438722 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]2[CH:6]=[CH:7][N:8]3[CH:14]=[CH:13][CH:12]=[C:9]3[C:10](=[O:11])[C:4]=2[CH:3]=1.Cl.[CH3:18][N:19](C)C=O>>[C:18]([C:2]1[CH:16]=[CH:15][C:5]2[CH:6]=[CH:7][N:8]3[CH:14]=[CH:13][CH:12]=[C:9]3[C:10](=[O:11])[C:4]=2[CH:3]=1)#[N:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 13141170HCID 13141170, compound

Product 1

HCID 131541969-cyano-11H-pyrrolo[2,1-b][3]benzazepin-11-one

Procedure

A stirred mixture of 1 gm. of 9-bromo-11H-pyrrolo[2,1-b][3]benzazepin-11-one, 1 gm. of cuprous cyanide and 5 ml. of dimethylformamide is heated to reflux for 5 hr. The mixture is then poured into a solution of 4 gm. of ferric chloride hydrate in 25 ml. of 2N hydrochloric acid. After stirring the resulting mixture at 60° for 30 min., it is extracted with 3 × 50 ml. of ethyl acetate, the organic extracts washed with 3 × 100 ml. of water and dried over Na2SO4. Evaporation of the dried solution yields 9-cyano-11H-pyrrolo[2,1-b][3]benzazepin-11-one.

Workup

  1. additionA stirred mixture of 1 gm
  2. temperatureto reflux for 5 hr
  3. additionThe mixture is then poured into a solution of 4 gm
  4. extractionit is extracted with 3 × 50 ml
  5. washof ethyl acetate, the organic extracts washed with 3 × 100 ml
  6. dry with materialof water and dried over Na2SO4
  7. customEvaporation of the dried solution

Sources & evidence

ORD record
ord-28122df547d748998f0de2c0bacd44d9
Source dataset
uspto-grants-1977_11
Patent number
US04056536

Reaction notes

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