Methyl 3-(hydroxymethyl)-5-[methyl(methylsulfonyl)amino]benzoate → Methyl 3-formyl-5-[methyl(methylsulfonyl)amino]benzoate

HRID 1160458Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]([CH3:18])[S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]>[O-2].[O-2].[Mn+4].C(OCC)(=O)C>[CH:2]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]([CH3:18])[S:14]([CH3:17])(=[O:15])=[O:16])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:1]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of methyl 3-(hydroxymethyl)-5-[methyl(methylsulfonyl)amino]benzoate obtained in Reference Example 21 1.10 g (4.0 mmol), manganese dioxide 3.38 g (39 mmol) and ethyl acetate (40 mL) was stirred at 70° C. for 2.5 hours. The mixture was filtered on Celite to remove the precipitates, and the solvent was concentrated to give 0.847 g (3.1 mmol) of the title compound (yield: 78%).

Workup

filtrationThe mixture was filtered on Celite
customto remove the precipitates
concentrationthe solvent was concentrated

Sources & evidence

ORD record: ord-b61bc49260da4fc68c8f8e713bb69359
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816387B2

Reaction notes

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