Sodium Hydroxide → Pranoprofen

HRID 1579451

Reaktionsgleichung

Reaktionsgleichung von HRID 1579451
Cl[C:2]([C:7]1[CH:8]=[CH:9][C:10]2[O:19][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH2:12][C:11]=2[CH:20]=1)([CH3:6])[C:3]([OH:5])=[O:4].[OH-].[Na+]>[Ni].[H][H]>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]2[CH2:12][C:11]3[CH:20]=[C:7]([CH:2]([CH3:6])[C:3]([OH:5])=[O:4])[CH:8]=[CH:9][C:10]=3[O:19][C:14]=12

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 215685142-chloro-2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid

Produkt 1

HCID 4888PranoprofenAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 178418361HCID 178418361, VerbindungLösungsmittel2×

Versuchsvorschrift

A mixture of 2.9 g of 2-chloro-2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid, 40 ml of 0.5 N aqueous sodium hydroxide solution and 1 g of Raney nickel is stirred in a hydrogen stream at ordinary pressure and temperature, until absorption of 230 ml of hydrogen is attained. The RAney nickel is then filtered off, and the filtrate is neutralized with hydrochloric acid. The crystalline precipitate is filtered off, washed with water, and recrystallized from aqueous dioxane to give 1.5 g of 2-(5H-[1]benzopyrano-[2,3-b]pyridin-7-yl)propionic acid melting at 183°-184°C.

Aufarbeitung

  1. filtrationThe RAney nickel is then filtered off
  2. filtrationThe crystalline precipitate is filtered off
  3. washwashed with water
  4. customrecrystallized from aqueous dioxane

Quellen und Nachweise

ORD-Eintrag
ord-e74532c36a8742fbac5be2082ad23742
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931205

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