Ammonia → 2-Chloro-6-methoxyquinolin-4-amine

HRID 2280499Notes

Reaction equation

HRID 2280499 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.CO.[NH3:17]>>[Cl:1][C:2]1[CH:11]=[C:10]([NH2:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 9483562,4-Dichloro-6-methoxyquinoline

Product 1

HCID 866899392-Chloro-6-methoxyquinolin-4-amineYield 55%

Conditions

Temperature
150 °C

Procedure

A suspension of 2,4-dichloro-6-methoxyquinoline (5.00 g, 22.0 mmol) in NH3 (g)/MeOH (saturated, 40 mL) was heated to 150° C. for 16 hours in a sealed tube. The solvent was removed and the residue was diluted with MeOH (20 mL). The mixture was filtered off and the filtrate was concentrated to give the crude product. Purification by column chromatography on silica gel (PE/EtOAc=2/1) gave product (7.50 g, yield: 55%) as a solid.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with MeOH (20 mL)
  3. filtrationThe mixture was filtered off
  4. concentrationthe filtrate was concentrated
  5. customto give the crude product
  6. customPurification by column chromatography on silica gel (PE/EtOAc=2/1)

Sources & evidence

ORD record
ord-98dbdc5c88324d018294d94083be9365
Source dataset
uspto-grants-2015_09
Patent number
US09139528B2

Reaction notes

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