Metoclopramide → Nicotinic Acid

HRID 614806

Reaktionsgleichung

Reaktionsgleichung von HRID 614806
CCN(CCN[C:9]([C:11]1[CH:12]=[C:13](Cl)[C:14]([NH2:19])=C[C:16]=1[O:17]C)=O)CC.P(Cl)(Cl)(Cl)=[O:22]>C(Cl)(Cl)Cl>[C:16]([OH:17])(=[O:22])[C:11]1[CH:12]=[CH:13][CH:14]=[N:19][CH:9]=1

Komponenten

4

Edukt 2

HCID 4168MetoclopramideHCID 24813Phosphorus oxychloride

Produkt 1

HCID 938Nicotinic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

(0.075 mole) and metoclopramide (14.9 grams; (0.95 mole) having the melting point of 148° C. are dissolved in 100 ml. of chloroform. At ambient temperature, 5.6 grams of phosphorous oxychloride are added drop by drop and the batch is heated for three more hours under reflux. After extraction with 80 ml. of 10% caustic soda solution, and subsequently with water, the chloroform solution is concentrated in a vacuum and the distillation residue having a boiling point of 100 to 140° C. is recrystallized from benzene. There is thus obtained 10.4 g. (51.4% of theory) of 4-nicotinoylamino-5-chloro-2-methyoxy-N-[2-(diethylamino)ethyl]benzamide having a melting point of 99° to 100° C.

Aufarbeitung

  1. dissolutionare dissolved in 100 ml
  2. temperaturethe batch is heated for three more hours
  3. temperatureunder reflux
  4. extractionAfter extraction with 80 ml
  5. concentrationof 10% caustic soda solution, and subsequently with water, the chloroform solution is concentrated in a vacuum
  6. customis recrystallized from benzene

Quellen und Nachweise

ORD-Eintrag
ord-7dfd2f859d3043ccbe159ecdd380bfc2
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04146637

Verknüpfte Notizen

Wird geladen…