Sodium Cyanide → Methyl 5-cyano-1-naphthoate

HRID 1166792

Reaction equation

HRID 1166792 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14][CH3:15])=[O:13].[C:16]([Cu])#[N:17].[C-]#N.[Na+]>CN(C=O)C.O>[C:16]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14][CH3:15])=[O:13])#[N:17]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 4557673Methyl 5-bromo-1-naphthoateHCID 178418546HCID 178418546, compound

Product 1

HCID 826304Methyl 5-cyano-1-naphthoateYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 5-bromo-1-naphthylcarboxylate (5.2 g, 19 mmol) and CuCN (3.4 g, 38 mmol) in 100 mL anhydrous DMF was refluxed overnight. After cooling the reaction to 70° C., a solution of NaCN (2 g) in 50 mL water was added to destroy the copper complex. Ethyl acetate was added and the two layers were separated. The organic layer was washed with brine, dried over MgSO4, and concentrated. Silica gel column chromatography using hexane/ethyl acetate (5/1) gave the product (3.8 g, 95%).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe reaction to 70° C.
  4. customto destroy the copper complex
  5. additionEthyl acetate was added
  6. customthe two layers were separated
  7. washThe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a4dd66e2a6f84475920f8b12515c57d9
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Linked notes

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