p-Toluidine → HCID 23333891, compound

HRID 2050201Notes

Reaction equation

HRID 2050201 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)([O:11][CH3:12])=[O:10]>C1(C)C=CC=CC=1>[C:9]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[N:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1)([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 23333891HCID 23333891, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-toluidine (0.20 moles), p-carbomethoxybenzaldehyde (0.20 moles), and IRC-50 (weakly acidic) ion exchange resin (0.5 g.) were azeotropically refluxed in toluene (150 cc.). The required amount of water had been removed after 3 hours. The solvent was removed on the rotary evaporator and the residue was recrystallized with 95% ethanol to yield N-(p-carbomethoxybenzylidene)-p-methylaniline.

Workup

  1. customThe required amount of water had been removed after 3 hours
  2. customThe solvent was removed on the rotary evaporator
  3. customthe residue was recrystallized with 95% ethanol

Sources & evidence

ORD record
ord-f14e69cfef4345e7ba464effb6a132d6
Source dataset
uspto-grants-1980_04
Patent number
US04200648

Reaction notes

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