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

HRID 1721509Notes

Reaction equation

HRID 1721509 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. Yield: 97.9%. m.p. 156°-161° C.; α!D25 -87.6° (C 0.7, CHCl3) NMR-spectral data (δ ppm, DMSO-d6) 1.48 (d) 3H; 4.34 (q) 1H; 6.75-7.9 (m) 9H;

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-2cbf731a4b8f43fa84aeda532ace43a5
Source dataset
uspto-grants-1996_04
Patent number
US05510519

Reaction notes

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