Dimethyl Sulfate → Methyl 2-amino-5-chlorobenzoate

HRID 1883190Notes

Reaction equation

HRID 1883190 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[CH3:12]OS(OC)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([O:9][CH3:12])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 124762-Amino-5-chlorobenzoic acid

Product 1

HCID 78878Methyl 2-amino-5-chlorobenzoateYield 96.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Chloroanthranilic acid (15.0 g), (CH3)2SO4 (11.6 g) and K2CO3 (12.7 g) were refluxed in acetone (150 g) for 30 minutes. The mixture was concentrated to about 90 g, and thereto was added water (90 g). The mixture was extracted with toluene (75 g), and the organic layer was concentrated to give methyl 5-chloroanthranilate (15.6 g, 96%).

Workup

  1. concentrationThe mixture was concentrated to about 90 g
  2. additionwas added water (90 g)
  3. extractionThe mixture was extracted with toluene (75 g)
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-a45c73a01c664c67a5a90c12b5c4893f
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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