HCID 4163245, compound → N-Phenethyl-benzene-1,4-diamine

HRID 1658447Notes

Reaction equation

HRID 1658447 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].CO>[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4163245HCID 4163245, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 2316538N-Phenethyl-benzene-1,4-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 15 g. of N-(2-phenylethyl)-p-nitroaniline, 100 ml. of methanol, and 2.5 g. of 10% palladium on carbon catalyst is shaken under 1 to 2 atmospheres of hydrogen until uptake of the hydrogen ceases. The resultant reaction mixture is filtered through celite and washed with methanol. The filtrate is concentrated in vacuo to yield the product, N-(2-phenylethyl)-p-phenylenediamine, as an oil which can be converted to the dihydrochloride, m.p. 247°C. by bubbling hydrogen chloride gas through a solution of the oil in ether for 1/2 hour.

Workup

  1. additionA mixture of 15 g
  2. customThe resultant reaction mixture
  3. filtrationis filtered through celite
  4. washwashed with methanol
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-dcc239e5b37b435fb91370e08c32847e
Source dataset
uspto-grants-1976_06
Patent number
US03963780

Reaction notes

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