Carbon Dioxide → Pranoprofen

HRID 1579452

Reaktionsgleichung

Reaktionsgleichung von HRID 1579452
[Mg].Br[CH:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:17][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH2:10][C:9]=2[CH:18]=1)[CH3:4].[C:19](=[O:21])=[O:20].Cl>O1CCCC1>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]2[CH2:10][C:9]3[CH:18]=[C:5]([CH:3]([CH3:4])[C:19]([OH:21])=[O:20])[CH:6]=[CH:7][C:8]=3[O:17][C:12]=12

Komponenten

6

Edukt 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 215685127-(1-bromoethyl)-5H-[1]benzopyrano[2,3-b]pyridine

Produkt 1

HCID 4888Pranoprofen

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A Grignard reagent is prepared from 0.31 g of metallic magnesium and 2.9 g of 7-(1-bromoethyl)-5H-[1]benzopyrano[2,3-b]pyridine in 10 ml of anhydrous tetrahydrofuran. To the Grignard reagent is added a large excess of dry ice. The mixture is allowed to stand overnight, and then poured into diluted hydrochloric acid. The precipitate is filtered off, and added to an aqueous sodium bicarbonate solution. An insoluble material is removed by filtration, and the filtrate is made acid with acetic acid. The resulting white crystals are collected and recrystallized from aqueous dioxane to give 2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid melting at 182.5°-183.5°C.

Aufarbeitung

  1. filtrationThe precipitate is filtered off
  2. additionadded to an aqueous sodium bicarbonate solution
  3. customAn insoluble material is removed by filtration
  4. customThe resulting white crystals are collected
  5. customrecrystallized from aqueous dioxane

Quellen und Nachweise

ORD-Eintrag
ord-776d6af16a82404cb92ca609a591bc22
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931205

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