Anthranilamide → HCID 13566148, compound

HRID 1033708Notes

Reaction equation

HRID 1033708 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>O>[CH2:22]([O:21][C:19]([CH2:18][NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 13566148HCID 13566148, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To 2 g of ortho-aminobenzamide were added 4.04 g (2 equivalents) of potassium carbonate, 4.94 g (2 equivalents) of ethyl bromoacetate, and the mixture was stirred under heating at 160° C. for 3 hours. After cooling to room temperature, water was added and the mixture extracted with ethyl acetate. After washing with aqueous sodium chloride, the mixture was dried over anhydrous magnesium sulfate, followed by evaporation of the solvent. The residue was developed with hexaneethyl acetate (1:2) by silica gel column chromatography to obtain 760 mg of the desired compound (yield 23.3%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture extracted with ethyl acetate
  3. washAfter washing with aqueous sodium chloride
  4. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  5. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-6859c112e49c426abcd69d49d00b04ea
Source dataset
uspto-grants-1994_05
Patent number
US05312625

Reaction notes

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