تفاعل #84104

ord-22a2dad257f1404186296a5281e81c61

معادلة التفاعل

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

الكواشف

لا شيء

ظروف التفاعل

درجة الحرارة
20°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصAqueous workup with EtOAc extraction
  2. 2
    أخرىgave the crude product
  3. 3
    أخرىPurification by silica gel column (PE/EtOAc=10/1 to 2/1)

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09433618B2uspto-grants-2016_09