6-Bromoquinoline → Quinoline-6-carbonitrile

HRID 333987ノート

反応式

HRID 333987 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:12]([Cu])#[N:13]>N1C=CC=CC=1>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:12]#[N:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 792436-BromoquinolineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 592995Quinoline-6-carbonitrile

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
200 °C

実験手順

To a stirred solution of 6-bromoquinoline (2.0 g, 9.61 mmol) in pyridine (30 mL) was added CuCN (3.0 g, 33.6 mmol) at RT under inert atmosphere. The reaction mixture was gradually heated to 200° C. and stirred for 8 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT, diluted with ice-cold H2O (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with H2O (50 mL) and brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography (eluting with 30% EtOAc/hexane) afforded compound I-C (1.25 g, 8.0 mmol, 83%) as white solid. 1H NMR (200 MHz, CDCl3): δ 9.08-9.05 (m, 1H), 8.25-8.19 (m, 3H), 7.86 (dd, J=8.6, 1.8 Hz, 1H), 7.55 (dd, J=8.6, 1.8 Hz, 1H). MS (ESI): 155 [M+H]+.

後処理

  1. customAfter complete consumption of the starting material (by TLC)
  2. temperaturethe reaction mixture was cooled to RT
  3. additiondiluted with ice-cold H2O (100 mL)
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic extracts were washed with H2O (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-8be3fcc2bcef4916b0310e101b56d938
出典データセット
uspto-grants-2014_11
特許番号
US08883797B2

反応ノート

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