Iodine → 2-Chloro-6-methoxyquinoline-3-carbonitrile

HRID 55826

Reaction equation

HRID 55826 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:14].O.II.C1[CH2:22][O:21]CC1>>[Cl:1][C:2]1[C:11]([C:12]#[N:14])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:21][CH3:22])[CH:8]=2)[N:3]=1

Participants

5

Reactant 4

HCID 807IodineHCID 8028TetrahydrofuranHCID 6909582-Chloro-3-quinolinecarboxaldehydeHCID 12896473Azane;hydrate

Product 1

HCID 8656122-Chloro-6-methoxyquinoline-3-carbonitrileYield 38%

Conditions

Temperature
20 °C

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.

Workup

  1. extractionAqueous workup with EtOAc extraction
  2. customgave the crude product
  3. customPurification by silica gel column (PE/EtOAc=10/1 to 2/1)

Sources & evidence

ORD record
ord-22a2dad257f1404186296a5281e81c61
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Linked notes

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