Hydrazine hydrate (1:1) → 8-Chloro-1-phenyl-3H-2-benzazepine hydrochloride

HRID 2295982Notes

Reaction equation

HRID 2295982 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][N:11]2[C:15](=O)[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3C2=O)=[C:4](C(=O)C2C=CC=CC=2)[CH:3]=1.O.NN>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:8]=[CH:9][CH2:10][N:11]=[C:15]([C:14]3[CH:13]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 539580771-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropene

Product 1

HCID 132717588-Chloro-1-phenyl-3H-2-benzazepine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6 g (15 mmole) of 1-[4-chloro-2-benzoylphenyl]-3-phthalimidopropene, 0.9 g (18 mmole) of 85% hydrazine hydrate and 70 ml of 95% ethanol was refluxed for 2.5 hr. The insoluble precipitate formed was separated by filtration. The filtrate was acidified with ice cold dilute hydrochloric acid and extracted with ether. The aqueous layer was separated, made alkaline with dilute sodium hydroxide and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate, acidified with methanolic hydrogen chloride, diluted with isopropanol and concentrated at reduced pressure to a small volume. The crude product was collected by filtration to give tan prisms, mp 223°-225° C. dec.

Workup

  1. temperaturewas refluxed for 2.5 hr
  2. customThe insoluble precipitate formed
  3. customwas separated by filtration
  4. extractionextracted with ether
  5. customThe aqueous layer was separated
  6. extractionextracted with methylene chloride
  7. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  8. additiondiluted with isopropanol
  9. concentrationconcentrated at reduced pressure to a small volume
  10. filtrationThe crude product was collected by filtration
  11. customto give tan prisms, mp 223°-225° C. dec.

Sources & evidence

ORD record
ord-b8bde9c9ce344ab780dd98c5597abfe6
Source dataset
uspto-grants-1984_01
Patent number
US04427589

Reaction notes

Loading…