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Hydrochloric Acid → 6-(3-Chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

HRID 1817336
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1817336
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16]([O:18]CC)=[O:17])=[N:11][CH:10]=[C:9]([OH:21])[C:8]=2[C:7]1=[O:22].[Li+].[OH-].Cl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16]([OH:18])=[O:17])=[N:11][CH:10]=[C:9]([OH:21])[C:8]=2[C:7]1=[O:22]
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Komponenten

7

Edukt 3

HCID 313Hydrochloric Acid2×HCID 3939Lithium HydroxideHCID 59455599Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Produkt 1

HCID 690584236-(3-Chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887
Methanol
Lösungsmittel
HCID 962WaterLösungsmittel2×
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (27.0 g, 71 mmol) in THF (333 mL) and MeOH (166 mL) was added LiOH (5.21 g, 214 mmol) dissolved in enough water to make a 1N solution (total volume 213 mL) and the reaction was heated to 60° C. overnight. HPLC showed completion. A white precipitate was observed. The reaction was neutralized with 1N HCl and the more volatile solvents removed, leaving the water solution. 300 mL water was added the solution was acidified to pH 1 with 1 N HCl. A large amount of solids had precipitated. The resulting slurry was stirred vigorously with 100 mL CHCl3. Most of the solid had precipitated from the partitioning and the entire mix was filtered and dried over the weekend to give product. Additional less pure product was recovered from extraction of the filtrate.

Aufarbeitung

  1. customthe more volatile solvents removed
  2. customleaving the water solution
  3. customA large amount of solids had precipitated
  4. customMost of the solid had precipitated from the partitioning and the
  5. additionentire mix
  6. filtrationwas filtered
  7. customdried over the weekend
  8. customto give product
  9. customAdditional less pure product was recovered from extraction of the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-db25fbb1b1d24769928dc3c548ebf0fc
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07598264B2

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