Sodium Cyanide → Methyl 5-cyano-1-naphthoate

HRID 1166792

반응식

HRID 1166792 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a4dd66e2a6f84475920f8b12515c57d9
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613942B1

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