Methanol → Methyl 3-amino-2-chlorobenzoate

HRID 851866Notes

Reaction equation

HRID 851866 reaction equation
[NH2:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[NH2:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4593153-Amino-2-chlorobenzoic acid

Product 1

HCID 15132848Methyl 3-amino-2-chlorobenzoateYield 92%

Procedure

A mixture of 3-amino-2-chlorobenzoic acid (500 mg, 2.91 mmol), conc. sulfuric acid (6 mL), and methanol (150 mL) was heated under reflux for 24 hours, and placed under reduced pressure to distill the solvent off. The residue was neutralized by addition of aqueous saturated sodium hydrogen carbonate. The neutralized mixture was extracted with toluene, dried over anhydrous magnesium sulfate, and placed under reduced pressure to distill the solvent off. There was obtained 497 mg (yield 92%) of the desired compound in the form of pale brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. distillationto distill the solvent off
  4. additionThe residue was neutralized by addition of aqueous saturated sodium hydrogen carbonate
  5. extractionThe neutralized mixture was extracted with toluene
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationto distill the solvent off

Sources & evidence

ORD record
ord-8384915723104d2898bd252e2dff13bf
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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