4-Hydroxybenzaldehyde → (-)-N-(p-hydroxybenzylidene)-1-(p-bromophenyl)ethylamine

HRID 488172

Reaction equation

HRID 488172 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1>C(O)C>[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[N:10][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH3:9])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 853000(R)-4-bromo-alpha-methylbenzylamine

Product 1

HCID 135802981(-)-N-(p-hydroxybenzylidene)-1-(p-bromophenyl)ethylamineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.44 g (0.0222 mole) of (R)-(+)-1-(p-bromophenyl)ethylamine and 2.85 g (0.0233 mole) of p-hydroxybenzaldehyde were dissolved in 30 ml of ethyl alcohol, and the solution thus formed was stirred under reflux for 3 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure, and refined by a column chromatography using 30 g of silica gel to give 6.75 g of (-)-N-(p-hydroxybenzylidene)-1-(p-bromophenyl)ethylamine.

Workup

  1. customthe solution thus formed
  2. temperatureunder reflux for 3 hours
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c85c00e039224d0fbdfb183b9c19d456
Source dataset
uspto-grants-1994_03
Patent number
US05298660

Linked notes

Loading…