- Production of Alprazolam
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(CAS NO.: ), with other name of 8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine, could be produced through many synthetic methods.
Following is one of the synthesis routes:


Firstly, 2,6-Dichloro-4-phenylquinoline (I) could react with refluxing hydrazine hydrate to produce 6-chloro-2-hydrazino-4-phenylquinoline (II) and then the yielding product is cyclocondensed with triethyl orthoacetate (A) in refluxing xylene yielding 7-chloro-1-methyl-5-phenyl-s-triazolo[4,3-a]quinoline (III). Next, the The oxidation of (III) to 5-chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)benzophenone (V) can be performed with sodium periodate and ruthenium dioxide in acetone-water, or first with ozone in CH2Cl2 affording 4-(2-benzoyl-4-chlorophenyl)-5-methyl-4H-1,2,4-triazol-3-carboxaldehyde (IV), which is then oxidized to (V) with silver oxide in methanol. Then the compound (V) is condensed with formaldehyde in xylene at 125 C to produce 5-chloro-2-(3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl)benzophenon (VI), which by reaction with PBr3 in chloroform is converted into 5-chloro-2-(3-bromoethyl-5-methyl-4H-1,2,4-triazol-4-yl)benzophenon (VII). Finally, this product is cyclized with ammonia in THF - methanol.
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