Acetic Acid → 5-Acetoxy-6-allyl-8-methylcarbostyril

HRID 1900712Notes

Reaction equation

HRID 1900712 reaction equation
[CH2:1]([C:4]1[C:5]([OH:16])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[NH:10][C:9](=[O:15])[CH:8]=[CH:7]2)[CH:2]=[CH2:3].[C:17](O)(=[O:19])[CH3:18]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:17]([O:16][C:5]1[C:4]([CH2:1][CH:2]=[CH2:3])=[CH:13][C:12]([CH3:14])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:15])[NH:10]2)(=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 233695765-Hydroxy-6-allyl-8-methylcarbostyril

Product 1

HCID 233696005-Acetoxy-6-allyl-8-methylcarbostyrilYield 91.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 6-allyl-5-hydroxy-8-methylcarbostyril (3.2 g, 14.9 mmol) in pyridine (50 ml), acetic acid (3.5 34.3 mmol) was added and stirred at room temperature for hour. The mixture was condensed and dissolved in chloroform. The resultant solution was washed with saturated aqueous sodium bicarbonate solution, aqueous 2N-HCl solution, and water, and dried and condensed. As a result, 3.5 g of 5-acetoxy-6-allyl-8-methylcarbostyril was obtained as colorless crystals (91.4%).

Workup

  1. customcondensed
  2. washThe resultant solution was washed with saturated aqueous sodium bicarbonate solution, aqueous 2N-HCl solution, and water
  3. customdried
  4. customcondensed

Sources & evidence

ORD record
ord-1a7f354d46e44a2f95bb1c21e03bcabc
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…