(Phenylmethyl)hydrazine → 1-benzyl-8-chloro-6-(2-chlorophenyl)-1H,4H-pyrazolo[4,3-d](2)benzazepine hydrochloride

HRID 268480Notes

Reaction equation

HRID 268480 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=O)[C:7](=[CH:18]N(C)C)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[CH2:25]([NH:32][NH2:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C>[ClH:1].[CH2:25]([N:32]1[C:6]2[C:5]3[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][C:4]=3[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:9][CH2:8][C:7]=2[CH:18]=[N:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 11157(Phenylmethyl)hydrazineHCID 536569248-Chloro-1-(2-chlorophenyl)-4-dimethylaminomethylidene-3,4-dihydro-2-benzazepin-5-one

Product 1

HCID 214316361-benzyl-8-chloro-6-(2-chlorophenyl)-1H,4H-pyrazolo[4,3-d](2)benzazepine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 0.72 g of 8-chloro-1-(2-chlorophenyl)-4-dimethylaminomethylidene-3,4-dihydro-2-benzazepin-5-one, 0.64 g of benzylhydrazine and 35 ml of ethanol is refluxed for 45 minutes and evaporated under reduced pressure. The residue is taken up in 20 ml methylene chloride, the solution washed with aqueous sodium bicarbonate and stirred with 6 ml of N hydrochloric acid for 20 minutes. The aqueous solution is made basic with sodium carbonate, the mixture stirred, the organic layer separated, dried and evaporated. The residue is taken up in the minimum amount of ethanol, the solution acidified with ethereal hydrogen chloride and the precipitate formed filtered off, to yield the 1-benzyl-8-chloro-6-(2-chlorophenyl)-1H,4H-pyrazolo[4,3-d](2)benzazepine hydrochloride melting at 218°-221°.

Workup

  1. temperatureis refluxed for 45 minutes
  2. customevaporated under reduced pressure
  3. washthe solution washed with aqueous sodium bicarbonate
  4. stirringthe mixture stirred
  5. customthe organic layer separated
  6. customdried
  7. customevaporated
  8. customthe precipitate formed
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-8543385e927444d79dfb7e7adf8de18d
Source dataset
uspto-grants-1976_03
Patent number
US03947585

Reaction notes

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