Hydrochloric Acid → 7-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

HRID 1410732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410732
[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]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 867141107-Benzyl-4-hydroxy-1-iodo-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl esterHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 682976087-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl esterAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturewas refluxed for 8 min
  2. extractionThe aqueous layer was extracted with additional CH2Cl2
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was chromatographed (0-10% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-cf433298c96746f0a058bc499866ea7b
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921389B2

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