Benzenamine, N-propyl- → 1-Phenyl-1-propylhydrazine

HRID 127958

Reaction equation

HRID 127958 reaction equation
[N:1]([N:3]([CH2:10][CH2:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.C(NC1C=CC=CC=1)CC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C:4]1([N:3]([CH2:10][CH2:11][CH3:12])[NH2:1])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 12153Benzenamine, N-propyl-HCID 12937302N-Phenyl-N-propylnitrous amideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 123271621-Phenyl-1-propylhydrazine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

N-nitroso-N-propylaniline, prepared from N-n-propylaniline by the same method as described in Example 1, was conveniently reduced with lithium aluminum hydride (LAH). The LAH in 450 ml dry ether was heated under reflux for 15 minutes, and a solution of 32.8 g (0.2 mol) crude 4 in 250 ml dry ether was added dropwise. The reaction mixture was allowed to stir for 3 hours before it was quenched by the dropwise addition of 12 ml water and 14 ml 20% sodium hydroxide. The resultant suspension was filtered free of inorganic salts, dried and stripped of solvents under diminished pressure. Distillation of the residue yielded the desired compound bp 55°-57°/0.12 mm.

Workup

  1. temperatureunder reflux for 15 minutes
  2. customwas quenched by the dropwise addition of 12 ml water and 14 ml 20% sodium hydroxide
  3. filtrationThe resultant suspension was filtered free of inorganic salts
  4. customdried
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-207580a4e11c40449621047bd2f67b3a
Source dataset
uspto-grants-1981_03
Patent number
US04258059

Linked notes

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