Water → HCID 57562912, compound

HRID 1725688Notes

Reaction equation

HRID 1725688 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:14]([O-])=O)[CH:8]=[C:9]([CH3:13])[C:10]=1[O:11][CH3:12])(=[O:4])=[O:3].[NH4+].[Cl-].O>C(O)C.[Fe]>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([CH3:13])[C:10]=1[O:11][CH3:12])[NH2:14])(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 57562885HCID 57562885, compound

Product 1

HCID 57562912HCID 57562912, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

The reduction of 3-aminosulfonyl-4-methoxy-5-methylnitrobenzene (0.740 g, 3 mmol) using iron powder (0.81 g, 15 mmol), NH4Cl (0.81 g, 15 mmol) in ethanol (100 mL): water (25 mL) at 60° C. for 1 hour followed by filtration through a pad of Celite gave aqueous alcoholic solution. Concentration of it followed by dilution with water afforded a solid mass, which was isolated by filtration to give 3-aminosulfonyl-4-methoxy-5-methylaniline. 1H NMR (DMSO-d6): δ 6.90 (bs, 1H), 6.55 (bs, 1H), 5.1 (bs, 2H), 3.65 (s, 3H), 2.15 (s, 3H), LCMS: purity: 94%, MS (m/e): 217 (MH+).

Workup

  1. filtrationwater (25 mL) at 60° C. for 1 hour followed by filtration through a pad of Celite
  2. customgave aqueous alcoholic solution
  3. customafforded a solid mass
  4. customwhich was isolated by filtration

Sources & evidence

ORD record
ord-c526a0a744434aec9b472cddc93b5eca
Source dataset
uspto-grants-2009_02
Patent number
US07491732B2

Reaction notes

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