Potassium Cyanide → HCID 84725891, compound

HRID 2204330Notes

Reaction equation

HRID 2204330 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4]([CH2:10]Br)[CH:3]=1.[C-:12]#[N:13].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O.C(Cl)Cl>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4]([CH2:10][C:12]#[N:13])[CH:3]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 867031384-Bromo-2-(bromomethyl)-5-methoxypyridine

Product 1

HCID 84725891HCID 84725891, compound

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 4-bromo-2-bromomethyl-5-methoxy-pyridine (Step AL2) (1.2 g, 4.3 mmol), KCN (417 mg, 6.4 mmol) and aliquat 336 (35 mg, 0.085 mmol) in H2O was stirred at 50° C. for 2 h. The reaction mixture was dissolved in CH2Cl2, extracted with a saturated aqueous solution of NaHCO3, washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (hexane/EtOAc, 100:0→1:1). tR: 3.83 min (HPLC 7).

Workup

  1. extractionextracted with a saturated aqueous solution of NaHCO3
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc, 100:0→1:1)

Sources & evidence

ORD record
ord-34a88bbcc41549bcacc92f45dc91fda3
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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