Ammonium Chloride → N~1~-Benzyl-4-nitrobenzene-1,2-diamine

HRID 1494323Notes

Reaction equation

HRID 1494323 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[N+:18]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].O.[S-2].[Na+].[Na+]>CO>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 346028N-Benzyl-2,4-dinitroanilineHCID 19906495Sodium sulfide monohydrate

Product 1

HCID 4381698N~1~-Benzyl-4-nitrobenzene-1,2-diamineYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2.0 g (7.3 mmol) N-benzyl-2,4-dinitroaniline, 1.50 g (28.0 mmol) ammonium chloride, 6.7 g (28.0 mmol) sodium sulfide hydrate and 100 ml methanol was refluxed for 3/4 h. After cooling to 25° C. the mixture was filtered and evaporated. The product was stirred with water to give 1.3 g (73%) N-benzyl-2-amino-4-nitroaniline. 1H-NMR (CDCl3): 8.1-6.5 (8H, m), 4.9-4.3 (3H, m), 3.4 (2H, broad s).

Workup

  1. temperaturewas refluxed for 3/4 h
  2. filtrationwas filtered
  3. customevaporated

Sources & evidence

ORD record
ord-f1861562c5b44c51bdfc43e399f0ff60
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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