Diethyl Ether → 1-(Isoquinolin-1-yl)ethan-1-one

HRID 748657

Reaction equation

HRID 748657 reaction equation
[C:1]1(C#N)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C[Mg]Br.CC[O:18][CH2:19][CH3:20]>C1COCC1>[C:1]1([C:19](=[O:18])[CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 3060571-IsoquinolinecarbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 131572141-(Isoquinolin-1-yl)ethan-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of isoquinoline-1-carbonitrile (Intemediate H1) (commercially available from Aldrich) (4.40 g, 28.5 mmol) in THF at 0° C. was treated with methylmagnesium bromide (20 mL, of a 3M soln in ether) for 3 h. (see procedure found in Vacher, B. et al J. Med. Chem. 1998 41, 5070; incorporated herein by reference). The mixture was quenched with a sat. solution of NH4Cl and stirred for 3 h at rt. The aqueous layer was basified with NaOH and extracted with ethyl acetate. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel with 10% ethyl acetate: hexane to give 1-isoquinolin-1-yl-ethanone (Intermediate H2) 3.65 g (75%).

Workup

  1. customThe mixture was quenched with a sat. solution of NH4Cl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe material was purified by chromatography on silica gel with 10% ethyl acetate

Sources & evidence

ORD record
ord-78ea6384b3db404a9266c767ef978e2d
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Linked notes

Loading…