Methanol → 3-Amino-2-nitrobenzoic acid

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[N+:1]([C:4]1[C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([O-])=O.[SH-].CO>O>[NH2:1][C:4]1[C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8]

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실험 절차

In one non-limiting reaction scheme, dinitrobenzoic acid may be reacted with about one to about five equivalents of an alkali hydrosulfide in a methanol:water mixture at reflux temperature for about 20 to about 40 minutes to produce an aminonitrobenzoic acid. As is described in the Example below, 2,6-dinitrobenzoic acid may be allowed to react with about three equivalents of sodium hydrosulfide in a methanol:water mixture at reflux temperature for about 30 minutes to produce 2-amino-6-nitrobenzoic acid. In some non-limiting embodiments, three equivalents of sodium hydrosulfide may be reacted with one equivalent of the sodium salt of 2,6-dinitrobenzoic acid in refluxing methanol/water followed by acidification.