Water → 2-Methylpyridine-3-carbonitrile

HRID 52365

반응식

HRID 52365 반응식
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C(Cl)Cl>[C:4]([C:3]1[C:2]([CH3:1])=[N:10][CH:9]=[CH:8][CH:7]=1)#[N:6]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 122437052-Methylnicotinamide

생성물 1

HCID 47383082-Methylpyridine-3-carbonitrile수율 75.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 2-methylnicotinamide from step 1 (11.1 g, 0.081 mol) in triethylamine (24.8 g, 0.243 mol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mol) rapidly at 0° C. The reaction was complete after a few minutes at this temperature. Water was added and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 7.2 g of 3-cyano-2methylpyridine as a pale yellow solid (75%): mp(DSC) 56°-58° C.

후처리

  1. waitThe reaction was complete after a few minutes at this temperature
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1)

출처 및 근거

ORD 기록
ord-9673fb8c9ca943f59b6b5e1aa4a9ca27
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616601

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