Toluene → Methyl 2-[(2-methylpentylidene)amino]benzoate

HRID 1283187Notes

Reaction equation

HRID 1283187 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:12][CH:13]([CH2:16][CH2:17][CH3:18])[CH:14]=O.C1(C)C=CC=CC=1>O>[CH3:11][O:10][C:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[N:4]=[CH:12][CH:13]([CH3:14])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8635Methyl AnthranilateHCID 312452-Methylpentaldehyde

Product 1

HCID 162595Methyl 2-[(2-methylpentylidene)amino]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

226.5 g (= 1.5 g mole) of methyl anthranilate, 150 g (= 1.5 g mole) of 2-methylpentanal and 400 g of toluene are brought into a 2 liter reaction flask. Then the mixture is agitated under reflux for about 5 hours at a bottom temperature of 100°-120°C, 20 g of water being taken off through the reflux head. Then the solution is concentrated at a 30 cm Vigreux column under reduced pressure (about 20 mm Hg) to a bottom temperature of 110°C. 360 g of toluene are obtained and 347 g of evaporation-residue. The evaporation residue is fractionated at a 30 cm Vigreux column to obtain:

Workup

  1. concentrationThen the solution is concentrated at a 30 cm Vigreux column under reduced pressure (about 20 mm Hg) to a bottom temperature of 110°C
  2. custom360 g of toluene are obtained
  3. customto obtain

Sources & evidence

ORD record
ord-1e222fe532cf4f78b565ecba0bd8d4a0
Source dataset
uspto-grants-1976_08
Patent number
US03974201

Reaction notes

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