2,4-Dinitrophenetole → 2,4-Diamino-1-ethoxybenzene

HRID 1415454Notes

Reaction equation

HRID 1415454 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][CH2:14][CH3:15])([O-])=O.[H][H]>NC1C(C)=CC=CC=1.O>[NH2:1][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 118872,4-DinitrophenetoleHCID 178418361HCID 178418361, compound

Product 1

HCID 499812,4-Diamino-1-ethoxybenzeneYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 7242O-ToluidineSolvent

Procedure

112 g (0.529 mol) of 2,4-dinitrophenetole were hydrogenated, in a 700 ml stirred autoclave, in 300 ml of o-toluidine with 15 g of water-moist palladium catalyst (0.5% by weight of palladium on charcoal), corresponding to 6 g of dry catalyst, at a temperature of about 80° C and a hydrogen pressure of between 5 and 10 bars. After 31/2 hours, the hydrogen absorption and the reaction had ended. After filtering off the catalyst, the solvent and the water of reaction formed were distilled off under normal pressure and the residue which remained was then fractionally distilled in vacuo. 71.7 g (89.3% of theory) of 2,4-diaminophenetole of solidification point 64.2° C were obtained in the boiling range of 150° - 180° C/5 mm Hg. 4.5 g of a higher-boiling residue remained.

Workup

  1. customat a temperature of about 80° C
  2. customAfter 31/2 hours, the hydrogen absorption
  3. filtrationAfter filtering off the catalyst
  4. customthe solvent and the water of reaction
  5. customformed
  6. distillationwere distilled off under normal pressure
  7. distillationthe residue which remained was then fractionally distilled in vacuo

Sources & evidence

ORD record
ord-7a7cdd4b93904f87b58c736e2d927bcf
Source dataset
uspto-grants-1977_01
Patent number
US04005143

Reaction notes

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