Hydrogen Peroxide → HCID 57748477, compound

HRID 906127Notes

Reaction equation

HRID 906127 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[C:4]=1[O:13][CH3:14])#[N:2].[OH-:15].[Na+].OO>CS(C)=O.C(O)C>[NH2:2][C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[C:4]=1[O:13][CH3:14])=[O:15]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67403735HCID 67403735, compound

Product 1

HCID 57748477HCID 57748477, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 22338741Dimethylsulfoxide ethanolSolvent

Procedure

To a solution of 4-cyano-2-methyl-3-(methyloxy)benzoic acid (80 mg, 0.42 mmol) in DMSO:ethanol (1:4, 1 mL) was added 1N aqueous sodium hydroxide (1 mL), and hydrogen peroxide (30% wt. in water, 1 mL). The mixture was stirred at room temperature for 72 hours, then partitioned between 1N aqueous sodium hydroxide and ethyl acetate and the organic layer discarded. The pH of the aqueous portion was adjusted to 7 using 1N aqueous hydrochloric acid. The aqueous portion was extracted several times using ethyl acetate, and the combined organic portion was washed with brine then dried over anhydrous sodium sulfate. Filtration and concentration afforded 55 mg, 0.26 mmol (63%) of 4-(aminocarbonyl)-2-methyl-3-(methyloxy)benzoic acid. 1H NMR (400 MHz, d6-DMSO): 7.77 (br s, 1H), 7.60 (br s, 1H), 7.54 (d, 1H), 7.41 (d, 1H), 3.72 (s, 3H), 2.41 (s, 3H). MS (EI) for C10H9NO3: 190 (M−H).

Workup

  1. custompartitioned between 1N aqueous sodium hydroxide and ethyl acetate
  2. extractionThe aqueous portion was extracted several times
  3. washthe combined organic portion was washed with brine
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-2a4cd100045f4ae5ac6b04bf1d5715a0
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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