n1-Isopropoxy-3-nitro-1-benzenesulfonamide → 3-Amino-n1-isopropoxy-1-benzenesulfonamide

HRID 29146Notes

Reaction equation

HRID 29146 reaction equation
[CH:1]([O:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)(=[O:8])=[O:7])([CH3:3])[CH3:2]>[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[NH2:15][C:11]1[CH:10]=[C:9]([S:6]([NH:5][O:4][CH:1]([CH3:3])[CH3:2])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 22997071n1-Isopropoxy-3-nitro-1-benzenesulfonamide

Product 1

HCID 229971243-Amino-n1-isopropoxy-1-benzenesulfonamideYield 96%

Reagents, catalysts & solvents 1

HCID 16218511Pd barium sulfateCatalyst

Procedure

To a Parr H2 vessel containing 5% Pd/BaSO4 (0.350 g) was added a methanolic solution (125 mL) of N1-isopropoxy-3-nitro-1-benzenesulfonamide (3.50 g, 0.0135 mol) at rt under Ar atm. The solution was hydrogenated at 45 psi for approx. 1.0 h. The reaction mixtire was filtered (½″ celite pad) and evaporated to give the product as yellow crystalline solid 2.90 g (96%). 1H NMR (CDCl3) 1.20(d,25H); 4.27(m, 1H); 7.05(s,1H); 7.75(1,1H); 8.22(d, 1H); 8.48 (dd,1H); 8.74(t, 1H).

Workup

  1. filtrationThe reaction mixtire was filtered (½″ celite pad) and
  2. customevaporated

Sources & evidence

ORD record
ord-909fd194f56d42fbac2af9f45fe97b81
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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