(4-Aminophenoxy)benzene → Ethyl 6-ethoxy-7-methyl-4-(4-phenoxyanilino)-1,8-naphthyridine-3-carboxylate hydrochloride
Reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:15])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[O:21]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[ClH:1].[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[N:7][C:8]=1[CH3:15])[N:5]=[CH:4][C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:2]2[NH:32][C:31]1[CH:30]=[CH:29][C:28]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:34][CH:33]=1)[CH3:14]Participants
3
Procedure
In a similar manner to Example 1, a mixture of ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate (1.93 g) and 4-phenoxyaniline (1.33 g) in IMS (40 ml) was boiled under reflux for 2 hours to give ethyl 6-ethoxy-7-methyl-4-(4-phenoxyanilino)-1,8-naphthyridine-3-carboxylate hydrochloride, m.p. 213°-215° C. Active (1/2) at 30 mg/kg.
Workup
- temperatureunder reflux for 2 hours
Sources & evidence
- ORD record
- ord-2361c4e8dc7c4f53bb0660c52271b342
- Source dataset
- uspto-grants-1995_11
- Patent number
- US05464781
Reaction notes
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