Hydrochloric Acid → 3-Ethoxy-2-methyl-5-[4-(2-pyridyloxy)anilino]-1,8-naphthyridine dihyrochloride trihydrate
Reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([O:13][CH2:14][CH3:15])[C:6]([CH3:12])=[N:7]2.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.[ClH:30]>>[OH2:13].[OH2:22].[OH2:13].[ClH:1].[ClH:30].[CH2:14]([O:13][C:5]1[C:6]([CH3:12])=[N:7][C:8]2[C:3]([CH:4]=1)=[C:2]([NH:27][C:26]1[CH:25]=[CH:24][C:23]([O:22][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=3)=[CH:29][CH:28]=1)[CH:11]=[CH:10][N:9]=2)[CH3:15]Participants
4
Procedure
A mixture of 5-chloro-3-ethoxy-2-methyl-1,8-naphthyridine (2.0 g) and 4-(2-pyridyloxy)aniline (1.67 g) in IMS (50 ml) was boiled under reflux for 3 hours and then allowed to stand at ambient temperature overnight. The mixture was evaporated under reduced pressure and the residue recrystallised from IMS to give a solid which was dissolved in hot IMS and then cooled in an ice bath while hydrogen chloride gas was bubbled through. The mixture was evaporated to dryness and the residue was recrystallised from IMS to give 3-ethoxy-2-methyl-5-[4-(2-pyridyloxy)anilino]-1,8-naphthyridine dihyrochloride trihydrate, m.p. 244°-247° C. Borderline active (1/1) at 30 mg/kg.
Workup
- temperatureunder reflux for 3 hours
- customThe mixture was evaporated under reduced pressure
- customthe residue recrystallised from IMS
- customto give a solid which
- customwas bubbled through
- customThe mixture was evaporated to dryness
- customthe residue was recrystallised from IMS
Sources & evidence
- ORD record
- ord-2a6aab8e9ce94a38955b36f526d554db
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05780482
Reaction notes
Loading…