Perchloric Acid → HCID 18975193, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[CH:8]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[O:7]C(C)C2.[CH3:23][C:24]([CH3:26])=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O.Cl(O)(=O)(=O)=O>>[CH2:23]([C:9]1([CH:4]=[CH:3][C:2]([Cl:1])=[C:11]([Cl:12])[CH2:10]1)[C:8]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:7])[C:24]([CH3:26])=[O:25]Participants
Procedure
4.75 g (14.0 mmoles) of the isochromane derivative prepared in Step A are oxidized according to the method of Example 1, Step B using Jones' reagent with the exception that instead of reacting the crude product with perchloric acid, the 1-acetonyl-3,4-dichloro-4'-nitrobenzophenone derivative (m.p.: 121°-122° C.) is isolated by chromatography. The solution of the above derivative in isopropanol is reacted with 98% hydrazine hydrate at 25° C. to obtain the monohydrazone derivative (m.p.: 167°-169° C.). The monohydrazone compound is reacted with methanol containing 15% hydrogen chloride, then, the hydrochloride of the title compound is treated with triethylamine to obtain the free base that is purified by recrystallization from hot dimethylformamide. M.p.: 231°-233° C.
Sources & evidence
- ORD record
- ord-109355dcb6844a7f81168760e4393c21
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05807851
Reaction notes
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