Ethyl 2-aminobenzoate → 2-[(Ethoxycarbonyl)amino]benzoic acid ethyl ester

HRID 1709980

Reaction equation

HRID 1709980 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O.O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:2]

Participants

6

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 10928Ethyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 41533612-[(Ethoxycarbonyl)amino]benzoic acid ethyl esterYield 98.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To an ice cooled solution of ethyl-o-aminobenzoate 1 (33 g, 0.2 mole) in acetone (270 ml) was added with stirring an ice cooled solution of potassium carbonate (36.7 g, 0.27 mole) in water (214 ml) followed by addition of ethyl chloroformate (43 g, 0.4 mole). Stirring was continued at 0° C. for 11/2 hour and at 25° C. for 2 hours. The mixture was poured in water (300 ml) and extracted with three 300 ml portions of ether. The combined and dried (MgSO4) ether phases were evaporated in vacuo to give pure 2 (46.7 g, 98%). The product was recrystallized (EtOH, H2O) to give colorless crystals, mp <40° C. (Calc. for C12H15NO4 : C 60.75; H 6.37; N 5.90). (Found C 60.75; H 6.29; N 5.85) 1H NMR (CDCl3) δ= 1.3 (3H, t, J=7 Hz) 1.4 (3H, t, J=7 Hz) 4.2 (2H, q, J=7 Hz) 4.3 (2H, q, J=7 Hz) 6.9-8.5 (4H, AA'BB'). IR (CCl4): 3300(m), 2980(m), 1735(s), 1690(s), 1600(s), 1510(w), 1450(s).

Workup

  1. customwas continued at 0° C. for 11
  2. custom2 hour
  3. extractionextracted with three 300 ml portions of ether
  4. dry with materialdried (MgSO4) ether phases
  5. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-13a5a5f03c734c9d991617993ffc4ea6
Source dataset
uspto-grants-1990_08
Patent number
US04952573

Linked notes

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