HCID 20300399, compound → N~1~-(Pentan-3-yl)benzene-1,2-diamine

HRID 1733153Notes

Reaction equation

HRID 1733153 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[NH:6][CH:7]([CH2:10][CH3:11])[CH2:8][CH3:9])([O-])=O.[H][H]>[Pd]>[CH2:8]([CH:7]([NH:6][C:5]1[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=1[NH2:1])[CH2:10][CH3:11])[CH3:9]

Participants

4

Reactant 2

HCID 20300399HCID 20300399, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20300411N~1~-(Pentan-3-yl)benzene-1,2-diamineYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a 2 liter Paar hydrogenator is placed 2.5 grams of 10% palladium on carbon catalyst, 800 milliliters of absolute alcohol and 250 grams of o-nitro-N-(1-ethylpropyl)aniline. Hydrogen is introduced and the reduction takes about 21/2 hrs. The reaction is exothermic and the temperature subsides as the reaction goes to completion. The catalyst is removed by filtration and the ethanol evaporated to yield a nearly quantitative yield (214 grams) of product as a dark oil. A pure sample is obtained by vacuum distillation b.p. 2.0 mm Hg=125°-126° C.

Workup

  1. custom2 hrs
  2. customThe catalyst is removed by filtration
  3. customthe ethanol evaporated

Sources & evidence

ORD record
ord-4db8d3ea38664b35b6e82e9ae77415d9
Source dataset
uspto-grants-1980_12
Patent number
US04240822

Reaction notes

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