Ammonium Chloride → HCID 58926755, compound
Reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[N:15]=2)[C:10](=[O:18])[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:8]1)=[O:6])([CH3:3])[CH3:2].[CH2:24]([Mg]Br)[CH3:25].[Cl-].[NH4+]>C1COCC1.[Cu]I>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[N:15]=2)[C:10](=[O:18])[CH:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]1[CH2:24][CH3:25])=[O:6])([CH3:2])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
Mix 7-methyl-4-oxo-4H-[1,8]naphthyridine-1,3-dicarboxylic acid 3-ethyl ester 1-isopropyl ester (1.21 g, 3.80 mmol) and copper(I) iodide (1.59 g, 8.36 mmol) in THF (75 ml). Cool the mixture to −78° C. Inject ethyl magnesium bromide (3.0 M in diethyl ether, 7.60 ml) and stir for 2 h. Warm up to −20° C. and keep the reaction at that temperature for 3 h. Pour the reaction mixture into saturated ammonium chloride solution (100 ml). Extract with ethyl acetate (3×100 ml). Combine the organic layers, dry over sodium sulfate, filter and concentrate. Purify using silica gel column chromatography (gradient eluent, 0-60% ethyl acetate in hexane) to provide 2-ethyl-7-methyl-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1,3-dicarboxylic acid 3-ethyl ester 1-isopropyl ester (0.715 g, 54%). MS (ES+): 349 (M+H).
Workup
- temperatureWarm up to −20° C.
- customthe reaction at that temperature for 3 h
- extractionExtract with ethyl acetate (3×100 ml)
- dry with materialCombine the organic layers, dry over sodium sulfate
- filtrationfilter
- concentrationconcentrate
- customPurify
Sources & evidence
- ORD record
- ord-fe9a664f21ad431f8b2aa311462de869
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470705B2
Reaction notes
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