Ethanol → 3-Methyl-4-nitrobenzene-1,2-diamine

HRID 355728Notes

Reaction equation

HRID 355728 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].C(O)C.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>O>[NH2:12][C:3]1[C:4]([NH2:5])=[CH:6][CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 73972Sodium sulfide nonahydrateHCID 824493-Methyl-2,4-dinitroaniline

Product 1

HCID 158959483-Methyl-4-nitrobenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-methyl-2,4-dinitroaniline (30 g, prepared by the procedure of A. J. Boulton, P. B. Ghosh, A. R. Katritzky, J. Chem Soc. (B), 1011 (1966)) in boiling ethanol (750 mL) is added dropwise over 90 minutes a solution of sodium sulfide nonahydrate (109.6 g) in water (750 mL). At the end of the addition, the mixture is refluxed for 30 minutes then poured in ice (2000g) and allowed to stand until all the ice has melted. The mixture is then extracted with methylene chloride and the organic layer is dried over magnesium sulfate and rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with methylene chloride to afford 2,3-diamino-6-nitrotoluene as an orange solid.

Workup

  1. additionAt the end of the addition
  2. temperaturethe mixture is refluxed for 30 minutes
  3. extractionThe mixture is then extracted with methylene chloride
  4. dry with materialthe organic layer is dried over magnesium sulfate and rotary evaporated
  5. customThe residue is purified by flash chromatography on silica gel
  6. washeluting with methylene chloride

Sources & evidence

ORD record
ord-f70c32189af944f89a1387d0a1a0dbab
Source dataset
uspto-grants-1998_11
Patent number
US05834470

Reaction notes

Loading…