Methyl 3-(methylsulfonamido)-5-nitrobenzoate → Methyl 3-amino-5-(methylsulfonamido)benzoate

HRID 1957960Notes

Reaction equation

HRID 1957960 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:5]=1>CO>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[C:6]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH:7]=[C:8]([NH2:10])[CH:9]=1

Participants

3

Reactant 1

HCID 57815097Methyl 3-(methylsulfonamido)-5-nitrobenzoate

Product 1

HCID 59243082Methyl 3-amino-5-(methylsulfonamido)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-methylsulfonylamino-5-nitro-benzoic acid methyl ester (32 g; 0.12 mol) was suspended in methanol (500 ml), 4 g (5% w/w; 4 g) was added and the mixture was hydrogenated at 4-5 bar. The reaction mixture was subsequently filtered on a Celite pad and the filtrate concentrated. 23 g (0.08 mmol; 66% yield) of a yellow powder were obtained.

Workup

  1. addition4 g (5% w/w; 4 g) was added
  2. filtrationThe reaction mixture was subsequently filtered on a Celite pad
  3. concentrationthe filtrate concentrated
  4. custom23 g (0.08 mmol; 66% yield) of a yellow powder were obtained

Sources & evidence

ORD record
ord-56b4fd4c9bb94bc69ffff4626f363f5f
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

Loading…