Formic Acid → 2,4-Dimethyl-3-nitroaniline

HRID 1106729Notes

Reaction equation

HRID 1106729 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[CH3:14])([O-:3])=[O:2].C(O)=O>[Pd].C(N(CC)CC)C.C(OCC)(=O)C>[CH3:14][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:9]([CH3:10])[CH:8]=[CH:7][C:6]=1[NH2:11]

Participants

6

Reactant 2

HCID 284Formic AcidHCID 690421,3-Dimethyl-2,4-dinitrobenzene

Product 1

HCID 133699632,4-Dimethyl-3-nitroaniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,6-dinitro-m-xylene (11.2 g) and 10% palladium on charcoal (620 mg) was stirred in triethylamine (36 mL) under an atmosphere of nitrogen and heated to reflux. Formic acid (9.25 mL) was added dropwise to the above mixture with vigorous stirring. After addition, the mixture was allowed to stir at reflux for an additional 15 min, then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (100 mL) and filtered through celite. The filtrate was washed with brine and dried over magnesium sulfate. Evaporation afforded 9.51 g as a yellow solid.

Workup

  1. temperatureheated to reflux
  2. additionAfter addition
  3. temperatureat reflux for an additional 15 min
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation
  8. customafforded 9.51 g as a yellow solid

Sources & evidence

ORD record
ord-8d2da1e7d1344a998216536d3cd91994
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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