Hydrochloric Acid → 7-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](I)[C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[C:25]([Cu])#[N:26].O.Cl>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 7-benzyl-4-hydroxy-1-iodo-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (136 mg, 0.31 mmol) and CuCN (56 mg, 0.62 mmol) in 5 mL of DMF was refluxed for 8 min. The mixture was cooled to r.t. and poured into a mixture of water and CH2Cl2. 4 M HCl was added to the mixture with vigorous stirring until no solid was present. The aqueous layer was extracted with additional CH2Cl2, and the combined organic layer was dried over MgSO4 and concentrated. The crude product was chromatographed (0-10% EtOAc/CH2Cl2) to give 88 mg of the title compound. MS: (+) m/z 336.00 (M+1).
Workup
- temperaturewas refluxed for 8 min
- extractionThe aqueous layer was extracted with additional CH2Cl2
- dry with materialthe combined organic layer was dried over MgSO4
- concentrationconcentrated
- customThe crude product was chromatographed (0-10% EtOAc/CH2Cl2)
Sources & evidence
- ORD record
- ord-cf433298c96746f0a058bc499866ea7b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921389B2
Reaction notes
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