Diethyl cyanophosphonate → 1-Isoquinolinecarbonitrile

HRID 44820

Reaction equation

HRID 44820 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N+:2]=1[O-].P([C:20]#[N:21])(=O)(OCC)OCC>C(#N)C>[C:1]1([C:20]#[N:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 76257Diethyl cyanophosphonateHCID 290378isoquinolin-N-oxide

Product 1

HCID 3060571-Isoquinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of isoquinoline 2-oxide (2-Im-9, 5.8 g) in 140 mL of acetonitrile, diethyl phosphoro-cyanidate (1.5 eq) was added under argon followed by slow addition of TEA (3.0 eq). The mixture was refluxed for 18 h and then extracted with DCM. The organic layer was concentrated and purified by silica column chromatography to give isoquinoline-1-carbonitrile (3-Im-9).

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. extractionextracted with DCM
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica column chromatography

Sources & evidence

ORD record
ord-9b95dfc3a79647eb97fd830507e6bf5e
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

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