Tetrahydrofuran → 1-(Isoquinolin-3-yl)ethan-1-one

HRID 931

Reaction equation

HRID 931 reaction equation
[CH3:1][Mg]Cl.[CH:4]1[C:13]2C(=[CH:9][CH:10]=[CH:11][CH:12]=2)C=C(C#N)[N:5]=1.[CH2:16]1[CH2:20][O:19][CH2:18][CH2:17]1>>[C:18]([C:17]1[N:5]=[CH:4][C:13]2[C:20]([CH:16]=1)=[CH:9][CH:10]=[CH:11][CH:12]=2)(=[O:19])[CH3:1]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 50768083-IsoquinolinecarbonitrileHCID 178418332HCID 178418332, compound

Product 1

HCID 112752751-(Isoquinolin-3-yl)ethan-1-oneYield 14%

Procedure

Methyl magnesium chloride (2.6 ml of a 3.0M solution in THF) was added dropwise to a solution of isoquinoline-3-carbonitrile at 0°-5° C. After the addition the reaction mixture was stirred at room temperature for 1 hour, then quenched with water. Hydrochloric acid (2M aqueous solution) was added to the reaction mixture until the aqueous phase was pH2. After stirring for 30 minutes the aqueous was neutralised with sodium bicarbonate (solid) and extracted with ether (×2). The combined extracts were washed with water, dried and concentrated to give a crystalline solid. Recrystalisation from hexane gave 3-acetyl-isoquinoline (0.55 g, 14% yield) as a pale yellow solid m.p. 84.4°-86.8° C. 1H NMR: 2.83(3H,s); 7.69-7.81(2H,m); 7.99(1H,m); 8.04(1H,m); 8.49(1H,m); 9.29(1H,s) ppm.

Workup

  1. additionAfter the addition the reaction mixture
  2. customquenched with water
  3. additionHydrochloric acid (2M aqueous solution) was added to the reaction mixture until the aqueous phase
  4. stirringAfter stirring for 30 minutes the
  5. extractionextracted with ether (×2)
  6. washThe combined extracts were washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto give a crystalline solid
  10. customRecrystalisation from hexane

Sources & evidence

ORD record
ord-1933fe9b9be74b32bfee65861da57c2d
Source dataset
uspto-grants-1998_03
Patent number
US05723473

Linked notes

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