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

HRID 1410624Notes

Reaction equation

HRID 1410624 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 in vacuo and the residue was diluted with MeOH (20 mL). The mixture was filtered off and the filtrate was concentrated to give the crude product, which was purified by column chromatography on silica gel (PE/EtOAc=2/1) to give 2-chloro-6-methoxyquinolin-4-amine (7.50 g, yield: 55%) as a yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  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, which
  6. customwas purified by column chromatography on silica gel (PE/EtOAc=2/1)

Sources & evidence

ORD record
ord-527bc9fe567d47d3ab1f56f2fea8dbb9
Source dataset
uspto-grants-2014_12
Patent number
US08921562B2

Reaction notes

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