Potassium Carbonate → 3,8-Dimethyl-5-(E-2-pentenyloxy)carbostyril

HRID 1900824Notes

Reaction equation

HRID 1900824 reaction equation
[CH3:1][C:2]1[C:3](=[O:14])[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][C:6]=2[CH3:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22]/[CH:23]=[CH:24]/[CH2:25][CH3:26]>CN(C)C=O>[CH3:1][C:2]1[C:3](=[O:14])[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH2:22]/[CH:23]=[CH:24]/[CH2:25][CH3:26])[CH:8]=[CH:7][C:6]=2[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 54630001-Bromo-2-pentene, predominantly transHCID 233696243,8-Dimethyl-5-hydroxycarbostyril

Product 1

HCID 233698243,8-Dimethyl-5-(E-2-pentenyloxy)carbostyrilYield 25.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,8-Dimethyl-5-hydroxycarbostyril (1.72 g, 9.1 mmol), potassium carbonate (2.51 g, 18.1 mmol), E-1-Bromo-2-pentene (2.0 g, 13.4 mmol) and dimethylformamide (30 ml) were allowed to react at 60° C. for 1 hour. After the completion of the reaction, the procedure described in Reference Example 31 was followed to obtain 0.60 g of the title compound as a colorless solid (25.6%).

Workup

  1. customto react at 60° C. for 1 hour
  2. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-d307188bfb0a4be8892f513c39e26b65
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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