Ammonia → 2-amino-3-nitro-5-methyl-N-(beta-hydroxyethyl)-aniline

HRID 2081895Notes

Reaction equation

HRID 2081895 reaction equation
[NH2:1][C:2]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([CH3:25])=[CH:18][C:3]=1[N:4]([CH2:15][CH2:16][OH:17])S(C1C=CC(C)=CC=1)(=O)=O.S(=O)(=O)(O)O.N>O>[NH2:1][C:2]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([CH3:25])=[CH:18][C:3]=1[NH:4][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric Acid2×HCID 197788282-amino-3-nitro-5-methyl-N-(beta-hydroxyethyl)-N-tosylaniline

Product 1

HCID 197788532-amino-3-nitro-5-methyl-N-(beta-hydroxyethyl)-aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.0458 mol (16.7 g) of 2-amino-3-nitro-5-methyl-N-(β-hydroxyethyl)-N-tosylaniline is introduced, whilst stirring, into 167 ml of concentrated sulphuric acid to which 48 ml of water has been added. The mixture is heated for 1 hour on a boiling water-bath and then poured onto 850 g of crushed ice. The sulphuric acid solution is neutralised with the aid of ammonia solution. The expected product precipitates. After filtration, washing with water, drying in vacuo and recrystallisation from ethanol, it melts at 166° C.

Workup

  1. additionhas been added
  2. temperatureThe mixture is heated for 1 hour on a boiling water-bath
  3. customThe expected product precipitates
  4. filtrationAfter filtration
  5. washwashing with water
  6. dry with materialdrying in vacuo and recrystallisation from ethanol, it melts at 166° C.

Sources & evidence

ORD record
ord-4e2cd8032b984fd2b676468ebb0caad6
Source dataset
uspto-grants-1993_02
Patent number
US05186717

Reaction notes

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