2-nitrobenzyl-N,N-dimethylsulfonamide → 2-aminobenzyl-N,N-dimethylsulfonamide
Reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)(=[O:5])=[O:4]>[Pd].COCCOCCOC>[CH3:1][N:2]([CH3:16])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13])(=[O:4])=[O:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In a pressure bottle, a mixture of 116 g of the product of Example 2, 1400 ml of 2-methoxyethyl ether and 10 g of 10% palladium on carbon was shaken at 110° under 500 p.s.i. hydrogen until the hydrogen was no longer absorbed. The catalyst was filtered off and the filtrate stripped under reduced pressure to a volume of 200 ml. This residue was poured into 600 ml of ice and the precipitate filtered off and dried to give 84 g of crude product, m.p. 70°-78°. Recrystallization from ~600 ml of 1-chlorobutane gave 60.6 g of N,N-dimethyl-2-aminobenzenemethanesulfonamide, m.p. 92°-100°.