Sodium hydride → 2-(3-Methoxybenzoyl)-4-oxo-4-pyridin-3-yl-butyronitrile

HRID 2121689Notes

Reaction equation

HRID 2121689 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([CH2:8][C:9]#[N:10])=[O:7].[H-].[Na+].Br.Br[CH2:18][C:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[O:20]>C1COCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([CH:8]([CH2:18][C:19](=[O:20])[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[C:9]#[N:10])=[O:7]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 5847163-(3-Methoxyphenyl)-3-oxopropanenitrileHCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Product 1

HCID 234341492-(3-Methoxybenzoyl)-4-oxo-4-pyridin-3-yl-butyronitrileYield 89.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 1.3 g (7.5 mmol) of 3-methoxybenzoyl acetonitrile in 30 mL of THF, cooled in a wet ice bath, was added 0.3 g (7.5 mmol) of sodium hydride (60% oil dispersion). After 1 h, added 1.0 g (3.6 mmol) of 3-bromoacetylpyridine hydrobromide. After 3 h, poured the reaction mixture into brine, extracted with ethyl acetate, dried over sodium sulfate, concentrated under reduced pressure and purified by flash chromatography (gradient elution: 40-100% ethyl acetate/hexane) to give 0.95 g (43%) of 2-(3-methoxybenzoyl)-4-oxo-4-pyridin-3-yl-butyronitrile (MH+=295).

Workup

  1. waitAfter 3 h
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography (gradient elution: 40-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1833d7185b404b4c873589aed57ebfd9
Source dataset
uspto-grants-2004_02
Patent number
US06696471B2

Reaction notes

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