Toluene → HCID 15745604, compound

HRID 2255064Notes

Reaction equation

HRID 2255064 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[N:7][CH:8]=1.[C:10]1([CH3:20])[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[CH:18]=O.C1(C)C=CC=CC=1>O>[CH3:20][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[CH:18]=[N:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 102542,4,6-TrimethylbenzaldehydeHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 15745604HCID 15745604, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5-aminomethyl-2-chloropyridine (14.25 g), mesitaldehyde (14.8 g) and toluene (100 ml) was heated under reflux for 3 hours. The water which was formed during the reaction was trapped by Dean and Stark constant water separator. The toluene was distilled off from the mixture under reduced pressure, so as to obtain N-(2,4,6-trimethylbenzylidene)-2-chloro-5-pyridylmethylamine (27 g). m.p. 47°-48° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe toluene was distilled off from the mixture under reduced pressure

Sources & evidence

ORD record
ord-de73be7b63a04a01aa7f96b89279d06e
Source dataset
uspto-grants-1993_08
Patent number
US05238949

Reaction notes

Loading…