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

HRID 2260721Notes

Reaction equation

HRID 2260721 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 3-methyl-2,4-dinitroaniline (30 g) 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 into ice (2000 g) 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-ec527a0c85d244ecb5c818e2b7b7259d
Source dataset
uspto-grants-1995_12
Patent number
US05478858

Reaction notes

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