Hydrochloric Acid → N,2-dihydroxy-4-methylbenzamide

HRID 501786Notes

Reaction equation

HRID 501786 reaction equation
Cl.[NH2:2][OH:3].[OH:4][C:5]1(O)[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][CH:6]1[C:7](OC)=[O:8].O.Cl>CO.C[O-].[Na+]>[OH:3][NH:2][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:13]([CH3:15])=[CH:14][C:5]=1[OH:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 68460751Methyl 2-hydroxy-4-methylsalicylate

Product 1

HCID 23021540N,2-dihydroxy-4-methylbenzamideYield 93.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 10942334Sodium MethoxideSolvent

Procedure

9.05 g of hydroxylamine hydrochloride was dissolved in 84 mL of methanol, to which 40.64 g of a 28% solution of sodium methoxide in methanol was added at room temperature, and then this mixture was stirred for 10 minutes. Then, 21 mL of a solution of 7.00 g of methyl 2-hydroxy-4-methylsalicylate in methanol was added dropwise to the reaction mixture, which was stirred for one hour at room temperature and then another four hours while heating it under reflux. The reaction mixture was added to water, and adjusted to pH 5 with 6M hydrochloric acid, and then resultant precipitate was filtered out thereof. The resultant solid was washed with water and diisopropyl ether successively to yield 5.95 g of N,2-dihydroxy-4-methylbenzamide as light yellow solid.

Workup

  1. additionwas added at room temperature
  2. stirringwas stirred for one hour at room temperature
  3. temperatureanother four hours while heating it
  4. temperatureunder reflux
  5. filtrationresultant precipitate was filtered out thereof
  6. washThe resultant solid was washed with water and diisopropyl ether successively

Sources & evidence

ORD record
ord-32eb6d56832a4e0baea64de037d2c7e5
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

Loading…