Benzocaine → Ethyl 4-((3-aminophenyl)amino)benzoate

HRID 1354973Notes

Reaction equation

HRID 1354973 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[NH2:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1.CCCCCC>C(OCC)(=O)C>[NH2:5][C:4]1[CH:3]=[C:2]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:19][CH:20]=2)[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 8058HexaneHCID 115623-Bromoaniline

Product 1

HCID 21106132Ethyl 4-((3-aminophenyl)amino)benzoateYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the general procedure, 3-bromoaniline (56 μL, 0.5 mmol) was coupled with ethyl 4-aminobenzoate (125 mg, 0.75 mmol) with the reaction temperature of 80° C. and the reaction time of 17 h. Chromatography on silica gel column with 4:1 hexane:ethyl acetate gave 55 mg (43%) of the title compound as a pale brown solid.

Workup

  1. customthe reaction time of 17 h

Sources & evidence

ORD record
ord-8cf587261ee648a18f3773729900bf6d
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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