Water → HCID 23152896, compound

HRID 1012279Notes

Reaction equation

HRID 1012279 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1[CH:18]=[CH:17]C=CC=1.C([CH:21]([CH2:25][C:26](Cl)=[O:27])[C:22](Cl)=[O:23])C.[OH2:29]>C1(C)C=CC=CC=1>[Cl:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:1][C:26](=[O:27])[CH2:25][CH2:21][C:22]([O:23][CH2:17][CH3:18])=[O:29])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 80001Methyl 4-chloroanthranilateHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 23152896HCID 23152896, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
10 °C

Procedure

To a solution of methyl 2-amino-4-chlorobenzoate (18.60 g, 100 mmol) and pyridine (11.5 ml, 142 mmol) in toluene (138 ml), was added dropwise a solution of ethyl succinyl chloride (18.9 ml, 133 mmol) in toluene (19 ml) at a temperature between 0° C. and 10° C. The mixture was stirred at 10° C. for 1 hr, water was added and the mixture was extracted with ethyl acetate. The organic layer was successively washed with 0.1N hydrochloric acid and 10% aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to give methyl 4-chloro-2-(3-ethoxycarbonylpropionylamino)benzoate (27.90 g, yield 89%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with 0.1N hydrochloric acid and 10% aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0ce9377b382540ba81f8431393adfd6e
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

Loading…