5-Chloro-2-methyl-1,8-naphthyridine → 2-Methyl-5-[4-(2-pyridyloxy)anilino]-1,8-naphthyridine hydrochloride hydrate
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[Cl:12])[N:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>>[OH2:19].[ClH:12].[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[NH:24][C:23]2[CH:22]=[CH:21][C:20]([O:19][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=3)=[CH:26][CH:25]=2)[N:3]=1Participants
Procedure
A mixture of 2-methyl-5-chloro-1,8-naphthyridine (2.0 g), 4-(2-pyridyloxy)aniline (2.1 g) and IMS (50 ml) was boiled under reflux for 3.5 hours. The mixture was cooled and filtered to give a solid. The solid was suspended in IMS (770 ml) and hydrogen chloride gas was bubbled through the mixture while the mixture was cooled in an ice bath. The mixture was then warmed until all the solid had dissolved and then cooled in an ice bath and further hydrogen chloride gas was bubbled through. After standing at 0° C. for 3 minutes, ethyl acetate (approximately 150 ml) was added and the precipitate was collected by filtration to give 2-methyl-5-[4-(2-pyridyloxy)anilino]-1,8-naphthyridine hydrochloride hydrate, m.p. 299°-305° C. Active (1/2) at 30 mg/kg.
Workup
- temperatureunder reflux for 3.5 hours
- temperatureThe mixture was cooled
- filtrationfiltered
- customto give a solid
- customhydrogen chloride gas was bubbled through the mixture while the mixture
- temperaturewas cooled in an ice bath
- temperatureThe mixture was then warmed until all the solid
- dissolutionhad dissolved
- temperaturecooled in an ice bath
- customfurther hydrogen chloride gas was bubbled through
- additionethyl acetate (approximately 150 ml) was added
- filtrationthe precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-c38cca1a2135492284b73ac5867b834a
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05780482
Reaction notes
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