Diphenyl Ether → HCID 178467175, compound

HRID 1580582Notes

Reaction equation

HRID 1580582 reaction equation
C(OC(=O)[CH2:5][C:6]([CH:8]=[CH:9][NH:10][C:11]1[O:15][N:14]=[C:13]([CH3:16])[CH:12]=1)=[O:7])C.[C:18]1([O:24]C2C=CC=CC=2)C=CC=CC=1>>[C:6]([C:8]1[C:18]([OH:24])=[C:12]2[C:13]([CH3:16])=[N:14][O:15][C:11]2=[N:10][CH:9]=1)(=[O:7])[CH3:5]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 68134469HCID 68134469, compound

Product 1

HCID 178467175HCID 178467175, compound

Procedure

23.8 g. of (3-methyl-5-isoxazolyl)aminomethyleneacetoacetic acid ethyl ester (0.1 mol.) are quickly added to 100 ml. of vigorously refluxing diphenyl ether. After 5 minutes, the reaction mixture is cooled, as rapidly as possible. After addition of 100 ml. diethyl ether, 5-acetyl-4-hydroxy-3-methylisoxazolo[5,4-b]pyridine crystallizes and is filtered off. Recrystallization from methanol yields 9.5 g. (49.5%) of pure product, m.p. 162°.

Workup

  1. temperaturethe reaction mixture is cooled
  2. additionAfter addition of 100 ml
  3. customdiethyl ether, 5-acetyl-4-hydroxy-3-methylisoxazolo[5,4-b]pyridine crystallizes
  4. filtrationis filtered off
  5. customRecrystallization from methanol
  6. customyields 9.5 g

Sources & evidence

ORD record
ord-f3f0b3c9f65b45358193b0a9ae60c590
Source dataset
uspto-grants-1976_01
Patent number
US03933823

Reaction notes

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