反応 #84104

ord-22a2dad257f1404186296a5281e81c61

反応方程式

O=Cc1cc2ccccc2nc1Cl
2-chloroquinoline-3-carboxaldehyde
C1CCOC1
THF
N.O
NH3.H2O
II
I2
COc1ccc2nc(Cl)c(C#N)cc2c1
product
収率 38.0%
COc1ccc2nc(Cl)c(C#N)cc2c1
2-chloro-6-methoxyquinoline-3-carbonitrile
収率 38.0%

反応条件

温度
20°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    抽出Aqueous workup with EtOAc extraction
  2. 2
    その他gave the crude product
  3. 3
    その他Purification by silica gel column (PE/EtOAc=10/1 to 2/1)

実験手順

To a mixture of 2-chloroquinoline-3-carboxaldehyde (1.00 g, 4.50 mmol) in THF (30 mL) was added NH3.H2O (30 mL, 25%) and I2 (1.26 g, 4.90 mmol), the mixture was stirred at 20° C. for 8 hours. Aqueous workup with EtOAc extraction gave the crude product. Purification by silica gel column (PE/EtOAc=10/1 to 2/1) gave the product (370 mg, yield 38%) as a yellow solid.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US09433618B2uspto-grants-2016_09