Acetic Anhydride → 2-[2-(Acetyloxy)phenyl][1,2]oxazolo[2,3-a]pyridin-8-ium bromide

HRID 328707Notes

Reaction equation

HRID 328707 reaction equation
[Br-:1].[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[O:17][N+:12]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:11]2[CH:10]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[Br-:1].[C:18]([O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[O:17][N+:12]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:11]2[CH:10]=1)(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 123521782-(2-Hydroxyphenyl)[1,2]oxazolo[2,3-a]pyridin-8-ium bromide

Product 1

HCID 123521952-[2-(Acetyloxy)phenyl][1,2]oxazolo[2,3-a]pyridin-8-ium bromideYield 73%

Procedure

2-(2-Hydroxyphenyl)isoxazolo[2,3-a]pyridinium bromide from Example 1 (5.0 g) is refluxed in acetic anhydride (40 ml) under nitrogen for 60-90 minutes. The solution is cooled, and the solvent is evaporated. The oily residue is diluted with ethyl acetate to crystallize the product. Recrystallization from isopropanol gives gray-white crystals (4.16 g, 73%), m.p. 198°-201° C.

Workup

  1. temperatureThe solution is cooled
  2. customthe solvent is evaporated
  3. additionThe oily residue is diluted with ethyl acetate
  4. customto crystallize the product
  5. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-9dd571565381450e8f75e50bd23eef57
Source dataset
uspto-grants-1977_04
Patent number
US04018781

Reaction notes

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