Methyl acetoacetate → 1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

HRID 1717339Notes

Reaction equation

HRID 1717339 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]=1[OH:15])=[N+:2]=[N-:3].O=[C:17]([CH3:23])[CH2:18][C:19]([O:21]C)=[O:20].[O-]CC.[Na+].[OH-].[Na+]>C(O)C>[CH2:11]([NH:10][C:8]([C:7]1[CH:13]=[CH:14][C:4]([N:1]2[C:17]([CH3:23])=[C:18]([C:19]([OH:21])=[O:20])[N:3]=[N:2]2)=[C:5]([OH:15])[CH:6]=1)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 2723922Sodium ethoxideHCID 866298074-azido-N-ethyl-3-hydroxybenzamide

Product 1

HCID 685161961-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-5-methyl-1H-1,2,3-triazole-4-carboxylic acidYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 4-azido-N-ethyl-3-hydroxybenzamide (0.41 g) obtained in Example 133b) and methyl 3-oxobutanoate (0.27 ml) in ethanol (10 ml) was added 28% sodium ethoxide in ethanol solution (1.0 ml) at room temperature, and the mixture was stirred overnight and at 60° C. for 9 hr. After allowing to cool to room temperature, 1N aqueous sodium hydroxide solution (4.0 ml) was added to the reaction mixture and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the obtained residue was diluted with water. The obtained aqueous solution was washed with ethyl acetate, acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude product of the title compound as a brown solid (0.32 g, 55%). The obtained crude product was used for the next reaction without further purification.

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture was stirred at room temperature overnight
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe obtained residue was diluted with water
  5. washThe obtained aqueous solution was washed with ethyl acetate
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-dc61466282f64fc4b88180528d4d791e
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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