3-(4-Aminophenoxy)-1,2-propanediol → Ethyl 6-ethoxy-4-[4-(2,3-dihydroxypropoxy)anilino]-1,5-naphthyridine-3-carboxylate
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH3:14])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[OH:20][CH:21]([CH2:31][OH:32])[CH2:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1>C(O)C>[CH2:13]([O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:2]2[NH:28][C:27]1[CH:29]=[CH:30][C:24]([O:23][CH2:22][CH:21]([OH:20])[CH2:31][OH:32])=[CH:25][CH:26]=1)[CH3:14]Participants
4
Procedure
A mixture of ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate (2.0 g), absolute ethanol (30 ml) and 4-(2,3-dihydroxypropoxy)aniline (1.38 g) was boiled under reflux for 1 hour. The reaction mixture was hot filtered and the filtrate evaporated to dryness. The residue was triturated with dichloromethane and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica using ethyl acetate as the mobile phase to give ethyl 6-ethoxy-4-[4-(2,3-dihydroxypropoxy)anilino]-1,5-naphthyridine-3-carboxylate, m.p. 143°-145° C.
Workup
- temperatureunder reflux for 1 hour
- filtrationThe reaction mixture was hot filtered
- customthe filtrate evaporated to dryness
- customThe residue was triturated with dichloromethane
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- customthe residue was purified by column chromatography on silica
Sources & evidence
- ORD record
- ord-601a862a1e2b42e4bb0d7989abad6ed0
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05780482
Reaction notes
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