Hydrochloric Acid → methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochloride

HRID 508571

Reaktionsgleichung

Reaktionsgleichung von HRID 508571
COC1C=CC(C[N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=3)[CH2:9]2)=CC=1.[ClH:23]>CO.[OH-].[OH-].[Pd+2]>[ClH:23].[CH2:9]1[C:10]2[C:15](=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2)[CH2:16][NH:8]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 58147238Methyl 2-(4-methoxybenzyl)isoindoline-5-carboxylate

Produkt 1

HCID 19828495methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochlorideAusbeute 2.242,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysator2×HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of methyl 2-(4-methoxybenzyl)isoindoline-5-carboxylate (0.82 g, 2.76 mmol) and 20% palladium hydroxide on carbon (0.194 g, 0.276 mmol) in methanol (25 mL) was added concentrated HCl (0.41 mL, 0.11 mmol). The mixture was degassed and stirred under a balloon atmosphere of H2 for two days. Additional 20% palladium hydroxide on carbon (0.08 g, 0.11 mmol) was then added and the reaction was continued for an additional day. The insolubles were removed via filtration through Clite and the solution was concentrated. Further drying under vacuum afforded a white powder (0.527 g, 91%). LCMS: (FA) ES+ 179. 1H NMR (d6-DMSO, 400 MHz) δ 9.71 (br s, 2H), 8.01 (s, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.55 (d, J=7.7 Hz 2H), 4.56 (d, J=6.0 Hz, 4H), 3.87 (s, 3H).

Aufarbeitung

  1. customThe mixture was degassed
  2. waitthe reaction was continued for an additional day
  3. customThe insolubles were removed via filtration through Clite
  4. concentrationthe solution was concentrated
  5. customFurther drying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-29d8c84632db486f9946cff7b9c082d5
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096518B2

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