Methyl (3-amino-4-nitrobenzenesulfonyl)acetate → Methyl (3,4-diaminobenzenesulfonyl)acetate

HRID 230735Notes

Reaction equation

HRID 230735 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>[Ni].CO>[NH2:1][C:2]1[CH:3]=[C:4]([S:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 57763327Methyl (3-amino-4-nitrobenzenesulfonyl)acetate

Product 1

HCID 57763314Methyl (3,4-diaminobenzenesulfonyl)acetate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

14.3 500 mg of Raney nickel are added to a solution of 2.40 g (8.76 mmol) of methyl (3-amino-4-nitrobenzenesulfonyl)acetate in 50 ml of methanol, and the mixture is hydrogenated at room temperature and atmospheric pressure. The catalyst is filtered off, and the filtrate is evaporated, giving methyl (3,4-diaminobenzenesulfonyl)acetate as a yellow solid; ESI 245.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-e6a8b9ab4a894c79b5517f3846aac74e
Source dataset
uspto-grants-2009_07
Patent number
US07566789B2

Reaction notes

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