Dimethylformamide → 5-Methylpicolinonitrile

HRID 431844

반응식

HRID 431844 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.ClCCl.[CH3:12][N:13](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.[Zn].Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]#[N:13])=[N:3][CH:4]=1

참가 물질

8

반응물 3

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 5642162-Bromo-5-methylpyridine

생성물 1

HCID 741835-Methylpicolinonitrile수율 56%

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-bromo-5-methylpyridine (2.001 g, 11.63 mmol), zinc cyanide (830 mg, 7 mmol), zinc (dust, 35 mg, 0.53 mmol), [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II), complex with dichloromethane (1:1) (192.5 mg, 0.24 mmol) in N,N-dimethylformamide (10 mL) was heated at reflux for 16 hours. After cooling, the reaction was diluted with ethyl acetate and extracted with water and brine. The organic solution was filtered through a plug of silica gel, washing dichloromethane. Removal of the solvent in vacuo, afforded 770 mg (56%) of 5-methyl-2-cyano-pyridine.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter cooling
  4. extractionextracted with water and brine
  5. filtrationThe organic solution was filtered through a plug of silica gel
  6. washwashing dichloromethane
  7. customRemoval of the solvent in vacuo

출처 및 근거

ORD 기록
ord-2e27af0b4bbc4ccf8085e124a9ccd2b1
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660753B2

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