Dimethylformamide → 5-Methylpicolinonitrile

HRID 431844

反応式

HRID 431844 の反応式
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

参加物

8

反応物 3

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

生成物 1

HCID 741835-Methylpicolinonitrile収率 56%

試薬・触媒・溶媒 4

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2e27af0b4bbc4ccf8085e124a9ccd2b1
出典データセット
uspto-grants-2003_12
特許番号
US06660753B2

関連ノート

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