Reaction #84104

Reaction equation

2-chloroquinoline-3-carboxaldehyde

THF

NH3.H2O

I2

→

product

Yield 38.0%

2-chloro-6-methoxyquinoline-3-carbonitrile

Yield 38.0%

Conditions

Workup

1. 1
   ExtractionAqueous workup with EtOAc extraction
2. 2
   Othergave the crude product
3. 3
   OtherPurification by silica gel column (PE/EtOAc=10/1 to 2/1)

Procedure

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.

Source