Methanol → 1-(3-Bromo-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

HRID 971089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971089
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([O:21]CC)=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.CO.[OH-].[Na+]>O1CCCC1.O.Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([OH:21])=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11057804Ethyl 1-(3-bromophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Produkt 1

HCID 223919781-(3-Bromo-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of ethyl 1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate from Step 2 (52.5 g, 140.7 mmol) in a mixture of tetrahydrofuran (400 mL), methanol (400 mL) and 1N aqueous sodium hydroxide (280 mL) was heated at ca 50° C. with stirring for 20 minutes. After cooling, the mixture was diluted with water (300 mL) and 1N aqueous HCl (325 mL) was added. After stirring for 45 minutes, the precipitate was filtered, washed well with water and dried to afford the title acid as a cream-colored solid.

Aufarbeitung

  1. temperaturewas heated at ca 50° C.
  2. temperatureAfter cooling
  3. additionwas added
  4. stirringAfter stirring for 45 minutes
  5. filtrationthe precipitate was filtered
  6. washwashed well with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d20892c560b34518b70d8695968d477e
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312334B2

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