2-(2-Acetylhydrazino)-7-chloro-5-phenyl-3H-1,4-benzodiazepine → Alprazolam

HRID 1764521Notes

Reaction equation

HRID 1764521 reaction equation
[C:1]([NH:4][NH:5][C:6]1[CH2:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:8]=2[N:7]=1)(=O)[CH3:2]>N1C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:8]2[N:7]3[C:1]([CH3:2])=[N:4][N:5]=[C:6]3[CH2:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]=2[CH:19]=1

Participants

3

Reactant 1

HCID 6243742-(2-Acetylhydrazino)-7-chloro-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 2118Alprazolam

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 3.3 parts of 2-(2-acetylhydrazino)-7-chloro-5-phenyl-3H-1,4-benzodiazepine prepared in Example 25 in 20 parts by volume of pyridine is refluxed, whereby the crystals are gradually dissolved. After 2 hours the solvent is evaporated under reduced pressure. The residue is recrystallized from a mixture of acetone and n-hexane to yield 8-chloro-1-methyl-6-phenyl-4H-s-triazolo [4,3-a] [1,4] benzodiazepine as colorless needles melting at 224° C to 225° C.

Workup

  1. temperatureis refluxed
  2. dissolutionwhereby the crystals are gradually dissolved
  3. customAfter 2 hours the solvent is evaporated under reduced pressure
  4. customThe residue is recrystallized from a mixture of acetone and n-hexane

Sources & evidence

ORD record
ord-3a04dc724e0145078b2891f0bdf0726c
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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