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

HRID 1957406Notes

Reaction equation

HRID 1957406 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-142e7f0f98df4dafb22f82d505a62750
Source dataset
uspto-grants-1998_07
Patent number
US05783589

Reaction notes

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