Water → HCID 69524486, compound

HRID 1178549Notes

Reaction equation

HRID 1178549 reaction equation
Br[C:2]1[C:3]([CH3:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[CH2:10]([Li])[CH2:11][CH2:12]C.C(#N)CC.[OH2:19]>C(OCC)C.CCCCCC>[CH3:9][C:3]1[C:2]([C:10](=[O:19])[CH2:11][CH3:12])=[CH:7][CH:6]=[C:5]([CH3:8])[N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7854PropionitrileHCID 6039713-Bromo-2,6-dimethylpyridineHCID 178418339Butyllithium

Product 1

HCID 69524486HCID 69524486, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

3-bromo-2,6-dimethyl-pyridine, (3.72 g, 20 mmol) were dissolved in 40 mL diethylether at −78° C. and treated with 10 mL of n-butyllithium (20 mmol) as a 2 M commercial solution in hexane. After stirring for 0.5 h, propionitrile (1.21 g, 22 mmol) was added and the mixture allowed to slowly warm to room temperature while stirring overnight. The mixture was then poured into water (0.5 volume equivalents relative to ether) and the mixture partitioned. The aqueous solution was extracted with ethyl acetate and the combined organic layers washed with water, dried with sodium sulfate, and concentrated in vacuo. Chromatography on silica using an ethyl acetate/hexane gradient gave the final product. Yield: 0.3 g (9%) 1H NMR (300 MHz, CDCl3), •1.18 (t, CH3, 3H), 2.56 (s, CH3, 3H), 2.68 (s, —CH3, 3H), 2.86 (q, CH2, 2H), 7.04 (d, Ar, 1H,), 7.8 (d, Ar, 1H).

Workup

  1. stirringwhile stirring overnight
  2. customthe mixture partitioned
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washthe combined organic layers washed with water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24dc4596a3a04805a84f4093533c4035
Source dataset
uspto-grants-2007_10
Patent number
US07276526B2

Reaction notes

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