Hydrochloric Acid → 5'-Propanoylspiro[cyclopropane-1,3'-indoline]-2'-one

HRID 2290507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2290507
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2([CH2:20][CH2:19]2)[C:11]1=[O:21].Cl>CN(C)C=O>[O:8]=[C:5]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11](=[O:21])[C:12]12[CH2:20][CH2:19]1)[CH2:6][CH3:7]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12701643Spiro(cyclopropane-1,3'-indolin)-2'-one

Produkt 1

HCID 137282955'-Propanoylspiro[cyclopropane-1,3'-indoline]-2'-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A slurry was made from 7.5 ml of dimethylformamide and 45.5 g of anhydrous aluminum chloride. The temperature rose to 40° C. and 2.97 ml of propionyl chloride and 5.43 g of spiro[cyclopropane-1,3'-[3H]-indol]-2'(1'H)-one were added. The mixture was stirred for 2 hours at 70° C. and was slowly poured into a mixture of ice and 50 ml of concentrated hydrochloric acid. After cooling overnight, the resulting precipitate was recovered by filtration. Crystallization from ethyl acetate provided 4.9 grams of the desired subtitle intermediate, m.p. 183°-185° C.

Aufarbeitung

  1. customrose to 40° C.
  2. temperatureAfter cooling overnight
  3. filtrationthe resulting precipitate was recovered by filtration
  4. customCrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ec65e0e591374a24ad9f28efa9ac0e20
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04617302

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