Pyridine → 5-Methoxyisophthalonitrile

HRID 431847노트

반응식

HRID 431847 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([NH2:14])=O)[CH:6]=[C:7]([CH:11]=1)[C:8]([NH2:10])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]#[N:14])[CH:6]=[C:7]([CH:11]=1)[C:8]#[N:10]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 21942402HCID 21942402, 화합물

생성물 1

HCID 219424235-Methoxyisophthalonitrile수율 46%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A suspension of the 5-methoxyisophthalamide (3.1 g, 16 mmol) in a dichloromethane (27 mL) at 0° C. was treated with pyridine (5.2 mL, 65 mol) and then trifluoroacetic anhydride drop-wise (5.4 mL, 39 mmol). The reaction was stirred at 0° C. for 20 minutes and then stirred overnight at ambient temperature. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. Silica gel chromatography using hexanes:ethyl acetate:dichloromethane afforded 940 mg (46%) of the 5-methoxyisophthalonitrile as a white solid.

후처리

  1. stirringstirred overnight at ambient temperature
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0d45eb141f164b05873630dcc9427728
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660753B2

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