Hydrochloric Acid → N-[2-methyl-3-(2-phthalimidylethyl)-1H-indol-5-yl]-4-fluoro-benzamide

HRID 365247

Reaktionsgleichung

Reaktionsgleichung von HRID 365247
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15]N)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[C:19]1(=[O:35])[N:23]([CH2:24][CH2:25][CH2:26][C:27](=O)[CH3:28])[C:22](=[O:30])[C:21]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:20]12.Cl.CCCCCC>C(O)C>[CH3:28][C:27]1[NH:15][C:12]2[C:13]([C:26]=1[CH2:25][CH2:24][N:23]1[C:22](=[O:30])[C:21]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:20]3[C:19]1=[O:35])=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]1[CH:17]=[CH:18][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:10][CH:11]=2

Komponenten

6

Edukt 4

HCID 313Hydrochloric Acid2×HCID 8058HexaneHCID 2362702-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dioneHCID 118316844-(4-Fluorobenzoyl)aminophenylhydrazine

Produkt 1

HCID 23290476N-[2-methyl-3-(2-phthalimidylethyl)-1H-indol-5-yl]-4-fluoro-benzamideAusbeute 6,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5.33 gm (21.7 mMol) 4-(4-fluorobenzoyl)aminophenylhydrazine and 5.03 gm (21.8 mMol) 5-phthalimidyl-2-pentanone in 100 mL ethanol were added 2 mL concentrated hydrochloric acid and the reaction mixture was heated at 80° C. for 14 hours. To the reaction mixture were then added an additional 3 mL concentrated hydrochloric acid and heating continued for an additional 6 hours. The reaction mixture was then cooled to 0° C. and 100 mL hexane were slowly added. The solid which formed was filtered and washed with hexane and provided, after drying, 6.67 gm of the desired compound. The mother liquor was concentrated under reduced pressure and then subjected to silica gel chromatography, eluting with 1:1 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide an additional 0.63 gm of product. Overall yield was 7.3 gm (76%).

Aufarbeitung

  1. temperatureheating
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customThe solid which formed
  4. filtrationwas filtered
  5. washwashed with hexane
  6. customprovided
  7. customafter drying
  8. concentrationThe mother liquor was concentrated under reduced pressure
  9. washeluting with 1:1 hexane
  10. additionFractions containing product
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ceff2496169e43e8ba9e7c79b5d28593
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06126932

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