Ethyl benzoylacetate → HCID 178434713, compound

HRID 1287646Notes

Reaction equation

HRID 1287646 reaction equation
C(O[C:4](=[O:14])[CH2:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[NH2:15][C:16]1[O:20][N:19]=[C:18]([CH3:21])[CH:17]=1>O>[CH3:21][C:18]1[C:17]2[C:4]([OH:14])=[CH:5][C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:15][C:16]=2[O:20][N:19]=1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 845905-Amino-3-methylisoxazole

Product 1

HCID 178434713HCID 178434713, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19.2 g. of benzoylacetic acid ethyl ester (0.1 mol.) are added dropwise to a stirred mixture of 9.8 g. of 5-amino-3-methylisoxazole (0.1 mol.) and 50 g. of polyphosphorous acid heated to 120°-125°. After the reaction has occurred, which can be recognized by changing of the color to brown, the reaction mixture is heated for an additional half hour at 125°. After the mixture has cooled to room temperature, 250 ml. of water are added in portions and stirring is continued until the compound becomes crystalline. The collected 3-methyl-6-phenylisoxazolo[5,4-b]pyridin-4-ol is washed with water, dried and recrystallized from ethanol yielding 19.9 g. (88%), m.p. 281°-282°.

Workup

  1. temperatureof polyphosphorous acid heated to 120°-125°
  2. temperatureis heated for an additional half hour at 125°
  3. washThe collected 3-methyl-6-phenylisoxazolo[5,4-b]pyridin-4-ol is washed with water
  4. customdried
  5. customrecrystallized from ethanol yielding 19.9 g

Sources & evidence

ORD record
ord-0bec0f9ea2054a9e81f3487fe7dd18d7
Source dataset
uspto-grants-1976_10
Patent number
US03985760

Reaction notes

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