3-Nitrobenzaldehyde → (E)-N-Butyl-1-(3-nitrophenyl)methanimine

HRID 1110344Notes

Reaction equation

HRID 1110344 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[N:1][CH2:4][CH2:11][CH2:10][CH3:9])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 74493-Nitrobenzaldehyde

Product 1

HCID 14971160(E)-N-Butyl-1-(3-nitrophenyl)methanimineYield 194.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 64 g (0.42 mole) 3-nitrobenzaldehyde in benzene was added 29.2 g of D-butylamine. The mixture was heated to reflux in a flask equipped with a Dean-Stark trap. After 90 minutes, the theoretical amount of water had separated, and the mixture was cooled and the solvent removed under vacuum, to give 84.4 g of N-(3-nitrobenzylidene)-1-butanamine.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux in a flask
  3. customequipped with a Dean-Stark trap
  4. customthe theoretical amount of water had separated
  5. temperaturethe mixture was cooled
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-8f37e620fb5f4726ac070daec9854d07
Source dataset
uspto-grants-1990_12
Patent number
US04975437

Reaction notes

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