Potassium Hydroxide → HCID 57748639, compound

HRID 906080Notes

Reaction equation

HRID 906080 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1)#[N:2].[OH-:13].[K+]>C(O)(C)(C)C.[Cl-].[Na+].O>[NH2:2][C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1)=[O:13]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 118193394-Cyano-2-methylbenzoic acid

Product 1

HCID 57748639HCID 57748639, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 4-cyano-2-methylbenzoic acid (0.071 g, 0.44 mmol) in 2 ml of t-butanol was added potassium hydroxide (0.13 g, 2.15 mmol). The reaction mixture was refluxed for 30 min and cooled to room temperature. To the reaction mixture was added 10 ml of brine and the reaction mixture was extracted with ethyl acetate (2×15 ml). The water layer was acidified to pH 1-2 with concentrated aqueous hydrochloric acid to give a white precipitate. The solid was collected by filtration, washed several times with water (3×15 ml) and dried in vacuo to provide 4-(aminocarbonyl)-2-methylbenzoic acid (0.038 g, 49% yield). 1H-NMR (400 MHz, DMSO-d6): 13.10 (br s, 1H), 8.07 (s, 1H), 7.87 (d, 1H), 7.78-7.72 (m, 2H), 7.50 (s, 1H), 2.54 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. extractionthe reaction mixture was extracted with ethyl acetate (2×15 ml)
  3. customto give a white precipitate
  4. filtrationThe solid was collected by filtration
  5. washwashed several times with water (3×15 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0b66483ba69f4e4c9e24c36b8f0d4741
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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