3-Methoxybenzaldehyde → 4-[(3-Methoxy-benzylidene)-amino]-benzoic acid methyl ester

HRID 2045395Notes

Reaction equation

HRID 2045395 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([N:10]=[CH:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH3:12])[CH:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 115693-MethoxybenzaldehydeHCID 12082Methyl 4-aminobenzoate

Product 1

HCID 9320964-[(3-Methoxy-benzylidene)-amino]-benzoic acid methyl esterYield 99.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture solution of 4-amino-benzoic acid methyl ester (10.0 g, 66.2 mmol), 3-methoxy-benzaldehyde (10.1 g, 72.7 mmol) and p-toluenesulfonic acid (225 mg, 1.32 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[(3-methoxy-benzylidene)-amino]-benzoic acid methyl ester (17.8 g, quant.) as a pale-white solid: MS calcd. for C16H15NO3 (M+H)+:270.3, obsd. (ESI+) [(M+H)+]270.1.

Workup

  1. temperatureto reflux for 12 hours
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with ether

Sources & evidence

ORD record
ord-1ea6ed59dd304fcc9b785a6e17e6e84a
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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