Dimethyl Sulfoxide → Benzoic acid, 2-amino-6-methyl-, methyl ester

HRID 864712

Reaction equation

HRID 864712 reaction equation
[OH-].[K+].CS(C)=O.[CH3:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([NH2:17])[C:13]=1[C:14]([OH:16])=[O:15].I[CH3:19]>CCOCC>[CH3:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([NH2:17])[C:13]=1[C:14]([O:16][CH3:19])=[O:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 1512106-Methylanthranilic acid

Product 1

HCID 583916Benzoic acid, 2-amino-6-methyl-, methyl esterYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Powdered potassium hydroxide (7.4 g, 0.132 mol) was admixed with dimethyl sulfoxide (DMSO) (100 ml), and the mixture was stirred for 5 minutes. 6-Methylanthranilic acid (10.0 g, 0.066 mol) was then added to the mixture and iodomethane (4.52 ml, 0.073 mol) added dropwise. The reaction mixture was stirred for 30 minutes at room temperature, then diluted with 250 ml of ether, washed with water (3×100 ml), dried over magnesium sulfate and concentrated. The crude product was filtered through a pad of flash grade (32-63) silica gel and eluted with 1:9 ether:hexane to afford 4.23 g (39%) of methyl 6-methylanthranilate as an oil.

Workup

  1. additionadded dropwise
  2. stirringThe reaction mixture was stirred for 30 minutes at room temperature
  3. washwashed with water (3×100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. filtrationThe crude product was filtered through a pad of flash grade (32-63) silica gel
  7. washeluted with 1:9 ether

Sources & evidence

ORD record
ord-b5ae44ad9b114018befd6bf62c2be929
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Linked notes

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