Benzocaine → 57707-09-2

HRID 1036905Notes

Reaction equation

HRID 1036905 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].[N+:13]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O)([O-:15])=[O:14]>C(O)C>[N+:13]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[N:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:12])=[CH:6][CH:7]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 111012-Nitrobenzaldehyde

Product 1

HCID 62454457707-09-2Yield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl-4-aminobenzoate (5.0 g, 30.3 mmol) in ethanol was added 2-nitrobenzaldehyde (5.03, 33.3 mmol) at room temperature. The reaction mixture was stirred at reflux for 3 h LC-MS showed ester was consumed nearly. The reaction mixture was concentrated in vacuo. The residue was washed by diethyl ether to give ethyl 4-(2-nitrobenzylideneamino)benzoate as yellow solid (7.8 g, yield 86.4%). LC/MS m/e obsd. (ESI+) [(M+H)+] 299.2.

Workup

  1. temperatureat reflux for 3 h LC-MS
  2. customwas consumed nearly
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washThe residue was washed by diethyl ether

Sources & evidence

ORD record
ord-ac2027e000ff4f458498a7a8685596cd
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

Loading…