Acetone → HCID 178518991, compound

HRID 2222586Notes

Reaction equation

HRID 2222586 reaction equation
[O:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]([OH:10])=[N:2]1.[CH2:11]([Br:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)=O>CN1C(=O)CCC1>[Br-:18].[CH2:11]([N+:7]1[CH:6]=[C:5]2[O:1][N:2]=[C:3]([OH:10])[C:4]2=[CH:9][CH:8]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 7498Benzyl BromideHCID 178518992HCID 178518992, compound

Product 1

HCID 178518991HCID 178518991, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of isoxazolo[5,4-c]pyridin-3-ol (50.0 g, 367 mmol) in NMP (100 ml) was added benzyl bromide (75.4 g, 441 mmol) dropwise rapidly. The thick solution was stirred for 24 h. The mixture was then added slowly to acetone (1.5 L) with stirring, and the solution was seeded. Stirring was continued at room temperature for 30 min, and then for a further 1 h in an ice/water bath. The mixture was filtered, the residue was washed with acetone and then dried under vacuum to give 6-benzyl-3-hydroxy-isoxazolo[5,4-c]pyridin-6-ium bromide (94.1 g, 83%; HPLC: 91% pure) as a white crystalline solid.

Workup

  1. stirringwith stirring
  2. stirringStirring
  3. waitwas continued at room temperature for 30 min
  4. waitfor a further 1 h in an ice/water bath
  5. filtrationThe mixture was filtered
  6. washthe residue was washed with acetone
  7. customdried under vacuum

Sources & evidence

ORD record
ord-afe93173041548a683189be45cdf3573
Source dataset
uspto-grants-2008_05
Patent number
US07371863B2

Reaction notes

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