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

HRID 1032776

반응식

HRID 1032776 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47355f03d7214ad3a0662f1cc36ceef2
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04959361

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