DEPROTECTION OF 2-PYRIDYL SULFONYL GROUP FROM PYRIDINE-2-SULFONAMIDES BY MAGNESIUM IN METHANOL

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• General Procedure: A solution of N,N-diphenylpyridine-2-sulfonamide (155 mg, 0.5 mmol) in dry methanol (4 ml) was added to Mg powder (122 mg, 5mmol) in an ice bath. The reaction mixture was stirred for 2 hr under a nitrogen atmosphere until the substrate disappeared by TLC. To the reaction mixture equal volumes of diethyl ether and saturated aqueous NH4Cl were added and the whole mixture was stirred for 2 hr. The organic layer was separated and the aqueous layer washed with ether. The combined organic layers were dried over MgSO4 and then concentrated in vacuo to give 81 mg (96%) of diphenylamine in almost pure form
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• According to TLC analysis, deacetylated product and BnNH2 appeared within 20 min. In order to compare with sonication condition, TsNAc(Bn) was subjected to reaction condition without sonication to give HN(Bn)-Ts(10 eq Mg/MeOH, rt, 20 min). Furthermore, complete deacetylation was observed within 5min when it was subjected to methanolic Mg(OMe)2
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