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

HRID 579334ノート

反応式

HRID 579334 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 867271556-Chloro-7-methoxyquinoline-2-carbonitrile収率 76.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-09de80e0cb474728bfacc03194212818
出典データセット
uspto-grants-2015_05
特許番号
US09040712B2

反応ノート

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