Ethanol → 4-(5-Cyclopropyl-1,2-oxazol-3-yl)pyridine

HRID 1076683Notes

Reaction equation

HRID 1076683 reaction equation
[CH:1]1([C:4]2(N3CCCC3)[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)[CH2:5]2)[CH2:3][CH2:2]1.C(O)C.Cl(O)(=O)(=O)=O.[OH-].[Na+]>O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 21537861HCID 21537861, compound

Product 1

HCID 123605774-(5-Cyclopropyl-1,2-oxazol-3-yl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.6 g. of 4-[5-cyclopropyl-5-(1-pyrrolidinyl)-2-isoxazolin-3-yl]pyridine in 25 ml. of ethanol is added 1.4 g. of 70% perchloric acid dissolved in 5 ml. of ethanol. This solution is diluted wth 25 ml. of water and heated on a steam bath for 1.0 hour. The solution is poured onto cracked ice, made basic with 10 N sodium hydroxide and filtered to collect straw-colored crystals, melting point 76°-80°C., nmr spectrum δ6.84 (DMSO-d6, s, 4-isoxazolyl H).

Workup

  1. additionThis solution is diluted wth 25 ml
  2. additionThe solution is poured
  3. filtrationfiltered
  4. customto collect straw-colored crystals, melting point 76°-80°C., nmr spectrum δ6.84 (DMSO-d6, s, 4-isoxazolyl H)

Sources & evidence

ORD record
ord-1b96da9ec77f4a558fc609c5e25e13aa
Source dataset
uspto-grants-1976_05
Patent number
US03957805

Reaction notes

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