Trimethylsilyl cyanide → 6-Chloro-7-methoxyquinoline-2-carbonitrile

HRID 579334노트

반응식

HRID 579334 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N+:8]([O-])=[CH:7][CH:6]=[CH:5]2.C[Si]([C:19]#[N:20])(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([C:19]#[N:20])[CH:6]=[CH:5]2

참가 물질

4

반응물 2

HCID 82115Trimethylsilyl cyanideHCID 867271566-Chloro-7-methoxyquinoline 1-oxide

생성물 1

HCID 867271556-Chloro-7-methoxyquinoline-2-carbonitrile수율 76.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

A 50 mL flask containing acetonitrile (6.0 mL) was charged with 6-chloro-7-methoxyquinoline 1-oxide (0.25 g, 1.19 mmol), TEA (0.33 mL, 2.39 mmol), and trimethylsilyl cyanide (0.48 mL, 3.58 mmol). The reaction mixture was heated at 80° C. for 2 h, cooled to room temperature and concentrated in vacuo. The residue was basified using saturated Na2CO3 and the product was extracted with DCM. The organic layer was dried with MgSO4, filtered and concentrated in vacuo to afford 6-chloro-7-methoxyquinoline-2-carbonitrile (0.20 g) MS [M+H+]=219.4.

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. extractionthe product was extracted with DCM
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-09de80e0cb474728bfacc03194212818
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040712B2

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