Acetic Acid → 5-[7-(4-Carboxyphenoxy)heptyl]-3-methylisoxazole

HRID 544610Notes

Reaction equation

HRID 544610 reaction equation
C(C1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[O:19][N:18]=[C:17]([CH3:20])[CH:16]=2)=[CH:5][CH:4]=1)#N.Cl.[C:24]([OH:27])(=[O:26])[CH3:25]>O>[C:24]([C:25]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[O:19][N:18]=[C:17]([CH3:20])[CH:16]=2)=[CH:5][CH:4]=1)([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 52712085-[7-(4-Cyanophenoxy)heptyl]-3-methylisoxazole

Product 1

HCID 52712095-[7-(4-Carboxyphenoxy)heptyl]-3-methylisoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0 g (0.01 mole) of 5-[7-(4-cyanophenoxy)heptyl]-3-methylisoxazole (Example 5), 20 ml of 20% aqueous hydrochloric acid and 20 ml of glacial acetic acid was heated at reflux for 19 hours. The reaction mixture was cooled, 20 ml of water added, and the solid product collected by filtration to give 3.0 g of 5-[7-(4-carboxyphenoxy)heptyl]-3-methylisoxazole as a colorless solid, m.p. 129°-130° C.; MIC vs. rhinovirus Type 2 in vitro=10 μg/ml.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 19 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe solid product collected by filtration

Sources & evidence

ORD record
ord-707ade732cdf4e6d862277323e126b53
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

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