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

HRID 1415455Notes

Reaction equation

HRID 1415455 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 97.3%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 7242O-ToluidineSolvent

Procedure

100 g (0.472 mol) of 2,4-dinitrophenetole were hydrogenated, in a 700 ml stirred autoclave, in 300 ml of o-toluidine with 12 g of water-moist palladium catalyst (1.0% by weight of palladium on active charcoal), corresponding to 4.8 g of dry catalyst, at about 80° C and a hydrogen pressure of between 5 and 10 bars. After about 23/4 hours, the hydrogen absorption and the reaction had ended. The catalyst was filtered off and the solvent and water of reaction were distilled off under normal pressure. 69.8 g (97.3% of theory) of crude 2,4-diaminophenetole of solidification point 63.5° C were obtained. The compound purified by distillation under reduced pressure had a solidification point of 64.2° C.

Workup

  1. customat about 80° C
  2. customAfter about 23/4 hours, the hydrogen absorption
  3. filtrationThe catalyst was filtered off
  4. customthe solvent and water of reaction
  5. distillationwere distilled off under normal pressure

Sources & evidence

ORD record
ord-4d1fa4e86c374bf880112041658af27a
Source dataset
uspto-grants-1977_01
Patent number
US04005143

Reaction notes

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