Citric Acid → 2-Benzoylamino-4-methoxy-3-methylbenzoic acid methyl ester

HRID 1443454Notes

Reaction equation

HRID 1443454 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH3:12])[C:5]=1[NH2:13].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH3:12])[C:5]=1[NH:13][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 7412Benzoyl chloride2×HCID 59165444Methyl 2-amino-4-methoxy-3-methylbenzoate

Product 1

HCID 684087382-Benzoylamino-4-methoxy-3-methylbenzoic acid methyl esterYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of the above ester (81) (1.5 g, 7.68 mmol) and TEA (2 ml) in dry DCM (30 ml) was added benzoyl chloride (1.4 g, 10 mmol) and the mixture was stirred for four hours at room temperature. Benzoyl chloride (0.14 g, 1 mmol) was added and the mixture was stirred for one hour more at room temperature. A 5% aqueous solution of citric acid was added and the mixture was extracted three times with ethyl acetate. The organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried with sodium sulfate and evaporated under reduced pressure. The product was purified by column chromatography on silica gel with eluted with hexane-ethyl acetate which gave the title compound (1.6 g).

Workup

  1. stirringthe mixture was stirred for one hour more at room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe product was purified by column chromatography on silica gel
  7. washwith eluted with hexane-ethyl acetate which

Sources & evidence

ORD record
ord-09259e93353d472a830439ee0fde0a7d
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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