Dimethylformamide → HCID 86639426, compound

HRID 1690209Notes

Reaction equation

HRID 1690209 reaction equation
I[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH3:10])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH3:12][N:13](C)C=O>>[OH:11][C:5]1[CH:4]=[CH:3][C:2]([C:12]#[N:13])=[N:7][C:6]=1[CH2:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 86639427HCID 86639427, compound

Product 1

HCID 86639426HCID 86639426, compoundYield 100%

Procedure

6-Iodo-2-propylpyridin-3-ol (2.0 g, 7.60 mmol) was dissolved in N,N-dimethylformamide (30 mL). Dinitrile zinc (1.34 g, 11.4 mmol) and tetrakis triphenylphosphine palladium (878 mg, 0.760 mmol) were added at room temperature, and the resultant mixture was stirred for 20 minutes under microwave irradiation. After completion of the reaction, the reaction solution was filtered using celite and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane/ethyl acetate) and 5-hydroxy-6-propyl picolinonitrile (1.75 g, yield >100%) was obtained as a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-c2a4d2546d89427eb264634b66096ade
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

Loading…