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Hydrochloric Acid → 4-Methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

HRID 1817343
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1817343
[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23]([O:25]CC)=[O:24])=[N:5][CH:4]=1.O.Cl>C1COCC1>[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23]([OH:25])=[O:24])=[N:5][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 67515740Ethyl 4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Produkt 1

HCID 690648344-Methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (15.2 g) in THF (150 mL) was added LiOH monohydrate (5.16 g) and sufficient water to dissolve the solids. The reaction was allowed to stir at room temperature for 1.5 hours. The reaction was neutralized with 125 mL of 1N HCl and the THF was removed in vacuo. The resulting slurry was partitioned between CHCl3 and 10% aqueous KHSO4. The combined organics were dried over sodium sulfate, filtered, and concentrated to dryness to afford the desired product as a pale tan foam. LRMS (M+1)=343.0

Aufarbeitung

  1. dissolutionto dissolve the solids
  2. customthe THF was removed in vacuo
  3. customThe resulting slurry was partitioned between CHCl3 and 10% aqueous KHSO4
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-537cf59db69248ccaeef4705726953ec
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07598264B2

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