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Sodium Hydroxide → HCID 178524772, Verbindung

HRID 1815885
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1815885
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:19])[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]([OH:20])=[N:6][CH:5]=1.[OH-].[Na+]>CO>[CH2:12]([NH:11][C:10]([C:8]1[C:7]([OH:20])=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([OH:21])=[O:2])=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 178498849HCID 178498849, Verbindung

Produkt 1

HCID 178524772HCID 178524772, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of 5-Benzylcarbamoyl-6-hydroxy-nicotinic acid methyl ester in methanol (20 ml) was added 5.2 ml (5.2 mmol) 1N NaOH. The mixture was heated to 50° C. and stirred overnight. Additional 1N NaOH was added (8.0 ml, 8.0 mmol). The mixture was heated to reflux for 6 hours. The mixture was allowed to cool and was stirred overnight. Methanol was removed by concentrating at reduced pressure. The resulting residue was dissolved in H2O and extracted with diethyl ether. The aqueous layer was acidified with 1M HCl and filtered. The solid product was washed with water and dried at reduced pressure overnight at 55° C. 1.2 g (85% yield). MS: m/z (APCI, AP+) 373.0 [M.]+. CHN Analysis: Calcd: C, 61.76; H, 4.44; N, 10.29. Found: C, 61.41; H, 4.42; N, 9.98.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. temperatureto cool
  4. stirringwas stirred overnight
  5. customMethanol was removed
  6. concentrationby concentrating at reduced pressure
  7. dissolutionThe resulting residue was dissolved in H2O
  8. extractionextracted with diethyl ether
  9. filtrationfiltered
  10. washThe solid product was washed with water
  11. customdried at reduced pressure overnight at 55° C

Quellen und Nachweise

ORD-Eintrag
ord-f788f7685f7243588d1812b7506bda4c
Quelldatensatz
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06881743B2

Notizen zur Reaktion

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