Methyl 4-aminobenzoate → HCID 178498125, compound

HRID 2407971Notes

Reaction equation

HRID 2407971 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.[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=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:16]/[C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([Br:12])[CH:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 765833-Bromobenzaldehyde

Product 1

HCID 178498125HCID 178498125, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

The mixture solution of 4-aminobenzoic acid methyl ester (10.8 g, 71.4 mmol), 3-bromo-benzaldehyde (13.3 g, 72.4 mmol) and p-toluenesulfonic acid (271.8 mg, 1.4 mmol) in toluene (150 mL) was heated to reflux for 12 h. 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-{[1-(3-bromo-phenyl)-meth-(E)-ylidene]amino}-benzoic acid methyl ester (22.6 g, quant.) as a light yellow solid: MS (ESI) M+1=318.0.

Workup

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

Sources & evidence

ORD record
ord-7b86f5e299d54cd58744fcb8adffc8cd
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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