Water → 1-(4-Benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylic acid

HRID 1029226

Reaktionsgleichung

Reaktionsgleichung von HRID 1029226
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:26]=[CH:25][N:24]=[C:23]3[C:18]=2[C:19]2[CH:31]=[CH:30][C:29]([C:32]([O:34]C)=[O:33])=[CH:28][C:20]=2[C:21](=[O:27])[NH:22]3)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].O>C1COCC1>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[CH:26]=[CH:25][N:24]=[C:23]3[C:18]=2[C:19]2[CH:31]=[CH:30][C:29]([C:32]([OH:34])=[O:33])=[CH:28][C:20]=2[C:21](=[O:27])[NH:22]3)=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 44205292Methyl 1-(4-benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylate

Produkt 1

HCID 442055041-(4-Benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylic acidAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

267 (220 mg, 0.47 mmol) and LiOH (56 mg, 2.37 mmol) were suspended in THF (2 mL) and H2O (2 mL) and stirred overnight at room temperature. The THF was removed, the mixture was diluted with H2O, and acidified to pH=5 with 1M HCl. The crude product was purified via HP-LC to provide 268 (120 mg, 56% yield) as a white solid. LC-MS (M+H=451, obsd.=451).

Aufarbeitung

  1. customThe THF was removed
  2. additionthe mixture was diluted with H2O
  3. customThe crude product was purified via HP-LC

Quellen und Nachweise

ORD-Eintrag
ord-f0597d8d52924da295458d42e70917b3
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735584B2

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