Methyl 4-aminobenzoate → HCID 178498130, compound

HRID 2407967Notes

Reaction equation

HRID 2407967 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.[F:12][C:13]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:14]=1[CH:15]=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:15]/[C:14]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:13]=2[F:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 178498130HCID 178498130, compoundYield 99.9%

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), 2,4-difluoro-benzaldehyde (10.3 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-(2,4-difluoro-phenyl)-meth-(E)-ylidene]amino}-benzoic acid methyl ester (19.64 g, quant.) as a light yellow solid: MS (ESI) M+1=276.1.

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-4a0685eb7b744ef69361c51b489884ec
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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