Dimethyl Sulfate → Benzoic acid, 2-amino-3-chloro-, methyl ester

HRID 1470711Notes

Reaction equation

HRID 1470711 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(OC)(O[CH3:16])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 808072-Amino-3-chlorobenzoic acid

Product 1

HCID 11030511Benzoic acid, 2-amino-3-chloro-, methyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

5.13 g (0.03 mol) of 2-amino-3-chlorobenzoic acid, ml of toluene, 0.97 g (0.003 mol) of tetrabutylammonium bromide, and 4.54 g (0.04 mol) of dimethyl sulfate were added to a 100 ml four-necked flask equipped with a stirrer, a reflux condenser, a thermometer, and a dropping funnel, and a mixture of 4.56 g (0.033 mol) of potassium carbonate and 9 ml of toluene was added dropwise with stirring at 80° C. Then, the mixture was stirred at 80° C. for 1 hour. The solution was analyzed by HPLC by the absolute calibration method, and as a result, the yield was 96%.

Workup

  1. customequipped with a stirrer, a reflux condenser
  2. additionwas added dropwise
  3. stirringThen, the mixture was stirred at 80° C. for 1 hour

Sources & evidence

ORD record
ord-f12928dbd62846498c176d9ec347d926
Source dataset
uspto-grants-2015_04
Patent number
US09006477B2

Reaction notes

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