Ammonia → 2-Chloro-6-methoxyquinolin-4-amine
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]=1Participants
4
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
- customThe solvent was removed
- additionthe residue was diluted with MeOH (20 mL)
- filtrationThe mixture was filtered off
- concentrationthe filtrate was concentrated
- customto give the crude product
- customPurification by column chromatography on silica gel (PE/EtOAc=2/1)
Sources & evidence
- ORD record
- ord-3d078d335c5d4208b8e5a167dfcb8f7b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921562B2
Reaction notes
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