Sodium Hydroxide → 3-(N-methylamino)aniline-4-sulfonic acid

HRID 257128Notes

Reaction equation

HRID 257128 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([NH:9][CH3:10])[C:7]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+].[H][H]>[Ni].O>[CH3:10][NH:9][C:8]1[CH:11]=[C:4]([CH:5]=[CH:6][C:7]=1[S:12]([OH:15])(=[O:14])=[O:13])[NH2:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 148330505-nitro-N-methylaniline-2-sulfonic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 109655703-(N-methylamino)aniline-4-sulfonic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

23.2 g of 5-nitro-N-methylaniline-2-sulfonic acid were added to 300 g of water. The pH was then adjusted to from 5. 0 to 5.5 with sodium hydroxide solution, 2 g of Raney nickel were added and hydrogenation was carried out under atmospheric pressure at 30° C. After hydrogen uptake had ceased, the catalyst was filtered off, the pH of the filtrate was adjusted to 0.5 to 1.0 with hydrochloric acid, and the precipitated 3-(N-methylamino)aniline-4sulfonic acid was isolated by filtration.

Workup

  1. customwas carried out under atmospheric pressure at 30° C
  2. filtrationthe catalyst was filtered off

Sources & evidence

ORD record
ord-30d7979674764d18a859cb61fe28bb96
Source dataset
uspto-grants-1993_11
Patent number
US05260431

Reaction notes

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