Dimethyl Sulfate → Methyl 4-amino-5-chloro-2-hydroxybenzoate

HRID 846599

Reaction equation

HRID 846599 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:12])[CH:3]=1.C[O-].[Na+].CO.S(OC)(O[CH3:22])(=O)=O>CO.O>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([O:8][CH3:22])=[O:7])=[C:4]([OH:12])[CH:3]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 148832224-Amino-5-chloro-2-hydroxybenzoic acidHCID 23694274Sodium methanolate methanol

Product 1

HCID 14883223Methyl 4-amino-5-chloro-2-hydroxybenzoateYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-amino-5-chloro-2-hydroxybenzoic acid (1.88 g, 0.010 mole) in absolute methanol (20 ml) was treated with 25% sodium methoxide/methanol (2.16 g, 0.010 mole), stirred for 30 minutes, and concentrated in vacuo. The solid residue was taken up in anhydrous acetone (30 ml), treated with dimethyl sulfate (1.64 g, 0.013 mole) and refluxed for 2 hours. The resultant solution was diluted with water (100 ml), and the precipitate was filtered, washed with water, and dried exhaustively in vacuo to afford 1.75 g (87%) of the title compound as fine colorless needles. The material was recrystallized from ethyl acetate/hexane; mp 138°-139° C.

Workup

  1. concentrationconcentrated in vacuo
  2. temperaturerefluxed for 2 hours
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried exhaustively in vacuo

Sources & evidence

ORD record
ord-b8028fed9620467b918409fb9488764d
Source dataset
uspto-grants-1992_08
Patent number
US05137895

Linked notes

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