Benzocaine → 4-[(5-Bromo-pyridin-3-ylmethylene)-amino]-benzoic acid ethyl ester

HRID 1801146Notes

Reaction equation

HRID 1801146 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=O)[CH:17]=[N:18][CH:19]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:20][C:16]2[CH:17]=[N:18][CH:19]=[C:14]([Br:13])[CH:15]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 2337BenzocaineHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 674404764-[(5-Bromo-pyridin-3-ylmethylene)-amino]-benzoic acid ethyl esterYield 101.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-amino-benzoic acid ethyl ester (16.5 g, 100 mmol), 5-bromo-pyridine-3-carbaldehyde (18.6 g, 100 mmol) and p-toluenesulfonic acid (380 mg, 2 mmol) in toluene (200 mL) was heated to reflux for 12 h. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[(5-bromo-pyridin-3-ylmethylene)-amino]-benzoic acid ethyl ester (33.8 g, quant.) as a light yellow solid: LC/MS m/e calcd for C15H13BrN2O2 (M+H)+: 334.19, observed: 332.9 & 335.0.

Workup

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

Sources & evidence

ORD record
ord-9563873ab8324b68a663da47cbb3bb2a
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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