Acetic Acid → 2-(Prop-2-yn-1-yl)isoquinolin-1(2H)-one

HRID 1032776

Reaction equation

HRID 1032776 reaction equation
[C:1]1([C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][NH:3]1)=[O:2].[K].[CH3:13][C:14](C)([O-])[CH3:15].C(Br)C#C.C(O)(=O)C>CN(C)C=O.O>[CH2:15]([N:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1]1=[O:2])[C:14]#[CH:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7842Propargyl bromideHCID 102841(2H)-IsoquinolinoneHCID 50987170Potassium tertbutoxide

Product 1

HCID 148519532-(Prop-2-yn-1-yl)isoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g (7 mmol) of isocarbostyril in 40 ml of dimethylformamide was treated with 0.86 g (7.7 mmol) of potassium-tert.-butoxide. After stirring under nitrogen for 30 minutes, 0.7 ml of propargyl bromide was added and stirring at room temperature was continued for 1 hour. The reaction mixture was acidified with acetic acid and diluted with water. The precipitated product was filtered off, washed with water and sucked dry. The residue was purified by chromatography over 30 g of silica gel using 5% (v/v) of ethanol in methylene chloride and crystallization from ether to give colorless crystals of 2-(2-propynyl)-1(2H)-isoquinolinone with m.p. 104°-105°. contains about. 0.125 molar amounts of H2O.

Workup

  1. stirringstirring at room temperature
  2. waitwas continued for 1 hour
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water
  5. customsucked dry
  6. customThe residue was purified by chromatography over 30 g of silica gel using 5% (v/v) of ethanol in methylene chloride and crystallization from ether

Sources & evidence

ORD record
ord-47355f03d7214ad3a0662f1cc36ceef2
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Linked notes

Loading…