Dimethyl Sulfoxide → 4-(Aminocarbonyl)-3-(cyclobutyloxy)benzoic acid

HRID 906106Notes

Reaction equation

HRID 906106 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[O:13][CH:14]1[CH2:17][CH2:16][CH2:15]1)#[N:2].CS(C)=[O:20].[OH-].[Na+].OO>C(O)C.O>[NH2:2][C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[O:13][CH:14]1[CH2:17][CH2:16][CH2:15]1)=[O:20]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67404284Methyl 4-cyano-3-(cyclobutyloxy)benzoate

Product 1

HCID 577484714-(Aminocarbonyl)-3-(cyclobutyloxy)benzoic acidYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4-cyano-3-(cyclobutyloxy)benzoate (0.051 g, 0.23 mmol) in 2 ml of ethanol was added 0.5 ml of DMSO, 1 ml of 1N aqueous sodium hydroxide, 1 ml of 30% aqueous hydrogen peroxide, and the reaction mixture was stirred at RT for 18 hrs. The reaction mixture was diluted with 10 ml of water and the aqueous solution extracted three times with ethyl acetate (20 ml). The aqueous layer was acidified to pH 3-4 by portion-wise addition of aqueous hydrochloric acid, then extracted with ethyl acetate (3×20 mL). The organic solution was rotary evaporated to dryness and dried in vacuo to provide 4-(aminocarbonyl)-3-(cyclobutyloxy)benzoic acid (0.026 g, 50%). 1H NMR (400 MHz, DMSO-d6): 13.25 (s, 1H), 7.80 (d, 1H), 7.68 (s, 1H), 7.63 (s, 1H), 7.55 (d, 1H), 7.41 (s, 1H), 4.88-4.85 (m, 1H), 2.44-2.43 (m, 2H), 2.18-2.14 (m, 2H), 1.99-1.73 (m, 2H). MS (EI) for C12H13NO4: 236 (MH+).

Workup

  1. extractionthe aqueous solution extracted three times with ethyl acetate (20 ml)
  2. additionThe aqueous layer was acidified to pH 3-4 by portion-wise addition of aqueous hydrochloric acid
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. customThe organic solution was rotary evaporated to dryness
  5. customdried in vacuo

Sources & evidence

ORD record
ord-382adc7161d947ab9eebc225752b4e6e
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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