Sodium sulfide nonahydrate → 3-Methyl-4-nitrobenzene-1,2-diamine

HRID 1936572Notes

Reaction equation

HRID 1936572 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].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>C(O)C.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 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 30 g of 3-methyl-2,4-dinitroaniline in 750 mL of boiling ethanol is added dropwise over 90 minutes a solution of 109.6 g of sodium sulfide nonahydrate in 750 mL of water. At the end of the addition, the mixture is heated to reflux 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 column 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 heated
  3. temperatureto reflux for 30 minutes
  4. extractionThe mixture is then extracted with methylene chloride
  5. dry with materialthe organic layer is dried over magnesium sulfate and rotary evaporated
  6. customThe residue is purified by flash column chromatography on silica gel
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-693d938a16ea48ee86a9fc553dfd517e
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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