Ammonia → 2-amino-3-nitro-N-methylaniline

HRID 2081900Notes

Reaction equation

HRID 2081900 reaction equation
[NH2:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][C:3]=1[N:4]([CH3:15])S(C1C=CC(C)=CC=1)(=O)=O.S(=O)(=O)(O)O.N>O>[NH2:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][C:3]=1[NH:4][CH3:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 19778848HCID 19778848, compound

Product 1

HCID 126202532-amino-3-nitro-N-methylaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

0.0716 mol (23 g) of 2-amino-3-nitro-N-methyl-N-tosylaniline is added gradually, in the course of 10 minutes whilst stirring, to 230 ml of concentrated sulphuric acid to which 23 ml of water has been added and which has been heated to 90° C. beforehand. When the addition has ended, the reaction medium is kept at 90° C. for 5 minutes and then poured onto crushed ice. The acid aqueous solution obtained is rendered alkaline with the aid of ammonia solution in order to precipitate the expected product. The latter is filtered off, washed with water and recrystallised from 40 ml of alcohol. After drying in vacuo, it melts at 93° C.

Workup

  1. additionhas been added
  2. additionWhen the addition
  3. additionpoured
  4. customonto crushed ice
  5. customThe acid aqueous solution obtained
  6. customto precipitate the expected product
  7. filtrationThe latter is filtered off
  8. washwashed with water
  9. customrecrystallised from 40 ml of alcohol
  10. customAfter drying in vacuo, it melts at 93° C.

Sources & evidence

ORD record
ord-7c7874cb51a649b980ae2587f0e120b3
Source dataset
uspto-grants-1993_02
Patent number
US05186717

Reaction notes

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