2-Hydroxyacetohydrazide → alpha-Hydroxyalprazolam

HRID 1199780Notes

Reaction equation

HRID 1199780 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[OH:20][CH2:21][C:22]([NH:24][NH2:25])=O>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:22]([CH2:21][OH:20])=[N:24][N:25]=[C:10]3[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 3505362-HydroxyacetohydrazideHCID 826706Thionordiazepam

Product 1

HCID 162244alpha-Hydroxyalprazolam

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In the manner given in Example 11, a solution of 1,3-dihydro-7chloro-5phenyl-2H-1,4-benzodiazepine-2-thione in n-butyl alcohol was heated to reflux with hydroxyacetic acid hydrazide to give 8-chloro-1-(hydroxymethyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of melting point 204°-206.5° C.

Sources & evidence

ORD record
ord-247d53bbcf4c4920a81cefd83e3aa5e1
Source dataset
uspto-grants-1990_02
Patent number
US04902794

Reaction notes

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