Potassium Cyanide → HCID 68442305, compound

HRID 1435875Notes

Reaction equation

HRID 1435875 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][N:12]=[C:13]3[C:18]=2[N:17]=[C:16]([O:19][CH3:20])[CH:15]=[CH:14]3)=[N:7][CH:8]=1.[C-:21]#[N:22].[K+]>CCO.O>[CH3:20][O:19][C:16]1[N:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[C:9]2[C:6]1[N:7]=[CH:8][C:3]([CH2:2][C:21]#[N:22])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 68442800HCID 68442800, compound

Product 1

HCID 68442305HCID 68442305, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 8-(5-bromomethylpyridin-2-yl)-2-methoxy[1,5]naphthyridine (0.70 g, 2.12 mmole), in EtOH (50 mL) at 60° C. was added KCN (0.21 g, 3.18 mmole) in H2O (3 mL). After 1.5 h, the reaction contents were cooled to RT and concentrated under vacuum. The aqueous residue was dissolved in EtOAc and washed with H2O, and dried over Na2SO4. Concentration under vacuum and purification on silica (EtOAc) afforded the title compound (0.38 g, 65%) as light yellow solid: LC-MS (ES) m/e 277 (M+H)+.

Workup

  1. customthe reaction contents
  2. concentrationconcentrated under vacuum
  3. dissolutionThe aqueous residue was dissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration
  7. customunder vacuum and purification on silica (EtOAc)

Sources & evidence

ORD record
ord-2bdcf22fb3a443d9a8d39ec3b3e8280e
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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