HCID 13022237, compound → 1,2,3-Triazolo(4,5-d)(2)benzazepine, 2,4-dihydro-8-chloro-6-phenyl-

HRID 1389033Notes

Reaction equation

HRID 1389033 reaction equation
[N:1]([CH2:4][C:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[C:17](=O)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:8][NH:7][N:6]=1)=[N+]=[N-].[H][H]>[Ni].C(O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]2[C:9]3[C:5](=[N:6][NH:7][N:8]=3)[CH2:4][N:1]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[CH:12]=1

Participants

5

Reactant 2

HCID 13022237HCID 13022237, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 30604461,2,3-Triazolo(4,5-d)(2)benzazepine, 2,4-dihydro-8-chloro-6-phenyl-Yield 76.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3 g (8.9 mmole) of 4-azidomethyl-5-[4-chloro-2-(benzoyl)phenyl]-2H-1,2,3-triazole and about 3 teaspoonsful of Raney nickel in 150 ml of ethanol was shaken in a Parr bottle with an initial hydrogen pressure of 5 p.s.i. for 1 hr. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to give 2 g of gummy solid. The residue was chromatographed over silica gel using a 1:1 mixture of ethyl acetate and methylene chloride as eluent. Evaporation of the solvent gave a gum which crystallized from a small amount of ethyl acetate to give white crystals. Recrystallization from a mixture of ethyl acetate and petroleum ether gave colorless prisms, mp 203°-205° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-2ad8dae8981d4e01a9fa2c8d82a7ad3b
Source dataset
uspto-grants-1981_01
Patent number
US04243589

Reaction notes

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