Thionyl Chloride → Methyl 3-aminophenylacetate

HRID 898151Notes

Reaction equation

HRID 898151 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1.[C:16](=O)(O)[O-].[Na+]>CO>[CH3:16][O:14][C:13](=[O:15])[CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([NH2:5])[CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 13054266Methyl 3-aminophenylacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methanol (20 mL) was cooled to −10 degrees under an atmosphere of argon. To the solvent was added dropwise thionyl chloride (4.31 mL) and a solution of 3-aminophenylacetic acid (3.00 g) in methanol (25 mL) and the mixture was stirred at −10˜0 degrees for 1 hour. To the reaction mixture was added saturated aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, and then concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to give the title compound (3.90 g) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-278e5b34dd7645e5bf82d32a26d36868
Source dataset
uspto-grants-2008_04
Patent number
US07351705B2

Reaction notes

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