4-Chloro-2,6-dinitroaniline → 5-Chloro-3-nitro-1,2-benzenediamine

HRID 54389Notes

Reaction equation

HRID 54389 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:5]([NH2:6])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([NH2:6])=[C:7]([NH2:9])[CH:8]=1

Participants

3

Reactant 1

HCID 214844-Chloro-2,6-dinitroaniline

Product 1

HCID 53610915-Chloro-3-nitro-1,2-benzenediamineYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
28 °C

Procedure

A suspension of 4-chloro-2,6-dinitroaniline (0.261 g, 1.19 mmol, Aldrich, used as received) in 6.66% aq. (NH4)2S (8.0 mL, prepared from 20% aq. solution available from Aldrich) and ethanol (8.0 mL) was refluxed for 45 min during which time it formed dark red solution. It was then cooled to 28° C. and the precipitated solid was filtered and dried under vacuum to yield 146 mg (65%) of pure 5-chloro-3-nitro-1,2-phenylenediamine as a shining red solid, 1H NMR (DMSO-d6): 5.031 (br s, 2H), 6.687 (br s, 2H), 6.912 (d, 1H, J=2.4 Hz), 7.413 (d, 1H, J=2.1 Hz).

Workup

  1. temperaturewas refluxed for 45 min during which time it
  2. customformed dark red solution
  3. filtrationthe precipitated solid was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0668157252eb4599aceeee8db2375826
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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