Benzaldehyde → Benzylaniline

HRID 1614430Notes

Reaction equation

HRID 1614430 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC=CC=1>[C:2]1([CH2:1][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 6115Aniline

Product 1

HCID 66028Benzylaniline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzaldehyde(31.84 g, 0.300 mol) and aniline (27.94 g, 0.300 mol) in benzene (100 ml) were heated to remove the water using a Dean-Stark trap. After 5.4 ml of water had been collected, the benzene was stripped off and the residual oil poured into a beaker. On treating with petroleum ether (10-20 ml) the oil crystallized. This mass was suction filtered and washed with some additional petroleum ether. Recrystallization from hexane gave off-white needles.

Workup

  1. customto remove the water using a Dean-Stark trap
  2. customAfter 5.4 ml of water had been collected
  3. additionthe residual oil poured into a beaker
  4. additionOn treating with petroleum ether (10-20 ml) the oil
  5. customcrystallized
  6. filtrationfiltered
  7. washwashed with some additional petroleum ether
  8. customRecrystallization from hexane
  9. customgave off-white needles

Sources & evidence

ORD record
ord-fb0d45b55f2446ae82b4dd4b1e1989fd
Source dataset
uspto-grants-1993_03
Patent number
US05196606

Reaction notes

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