Acetonitrile → 3-(Isoquinolin-6-yl)-3-oxopropanenitrile

HRID 598835Notes

Reaction equation

HRID 598835 reaction equation
[C:1](#[N:3])[CH3:2].C([Li])(C)(C)C.[CH:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([O:21]C)=O)=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1>C1COCC1>[CH:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19](=[O:21])[CH2:2][C:1]#[N:3])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 152903606-Isoquinolinecarboxylic acid, methyl esterHCID 178418306HCID 178418306, compound

Product 1

HCID 579505683-(Isoquinolin-6-yl)-3-oxopropanenitrileYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ACN (1.8 g, 43 mmol) in 90 mL of THF at −78° C. was added tert-butyllithium (25 mL, 1.7 M in heptane). After 20 minutes, methyl isoquinoline-6-carboxylate (2.0 g, 11 mmol) was added slowly in 10 mL of THF. After 1 hour, the reaction was quenched with 100 mL of aqueous NH4Cl and warmed to room temperature. The biphasic mixture was extracted twice with 100 mL of EtOAc, and the combined organic extracts were washed with 100 mL of brine and dried over MgSO4. Filtration and concentration under reduced pressure afforded 3-(isoquinolin-6-yl)-3-oxopropanenitrile (2.1 g, 100% yield crude). The product thus obtained was used in the next step without any further purification.

Workup

  1. waitAfter 1 hour
  2. customthe reaction was quenched with 100 mL of aqueous NH4Cl
  3. extractionThe biphasic mixture was extracted twice with 100 mL of EtOAc
  4. washthe combined organic extracts were washed with 100 mL of brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-226bf91ae26b4e42a0520fc7d03d62e4
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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