Methanol → Benzoic acid, 2-amino-3-chloro-, methyl ester

HRID 1470713Notes

Reaction equation

HRID 1470713 reaction equation
[CH3:1]O.S(Cl)(Cl)=O.[NH2:7][C:8]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]>>[NH2:7][C:8]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([O:12][CH3:1])=[O:11]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 808072-Amino-3-chlorobenzoic acid

Product 1

HCID 11030511Benzoic acid, 2-amino-3-chloro-, methyl esterYield 61%

Conditions

Temperature
-5 °C

Procedure

3 ml (0.074 mol) of methanol was added to a 50 ml four-necked flask equipped with a stirrer, a reflux condenser, a thermometer, and a dropping funnel, and 1.43 g (0.012 mol) of thionyl chloride was added dropwise with stirring at −5° C. Then, a mixture of 1.71 g (0.010 mol) of 2-amino-3-chlorobenzoic acid in 2.0 ml (0.049 mol) of methanol was added dropwise with stirring at −5° C. Then, the mixture was stirred at room temperature for 15 hours and at 65° C. for 17 hours. The reaction solution was analyzed by HPLC by the absolute calibration method, and as a result, the yield was 61%.

Workup

  1. customequipped with a stirrer, a reflux condenser
  2. additionwas added dropwise
  3. stirringwith stirring at −5° C
  4. stirringThen, the mixture was stirred at room temperature for 15 hours and at 65° C. for 17 hours

Sources & evidence

ORD record
ord-130ece94cec94e9aa3911329b7374fa7
Source dataset
uspto-grants-2015_04
Patent number
US09006477B2

Reaction notes

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