Hydrochloric Acid → 4-(1,3-Dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylic acid

HRID 1944722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944722
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][C:15]([CH3:23])([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]1.Cl>C(O)(=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][C:15]([CH3:23])([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 58074352Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate2×

Produkt 1

HCID 580743564-(1,3-Dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylic acidAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate (Intermediate 72, 900 mg, 2.85 mmol) was added to 6M aq. hydrochloric acid (0.951 mL, 5.71 mmol) in acetic acid (5 mL). The reaction mixture was heated to 90° C. for 48 h and then concentrated under vacuum. The residue was taken up in a minimal volume of ethyl acetate and a white solid precipitated. The solid was collected by filtration, washed with acetonitrile and dried to provide the product acid (475 mg) as a white solid. LCMS [M−H]=286.3

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customa white solid precipitated
  3. filtrationThe solid was collected by filtration
  4. washwashed with acetonitrile
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c772fef17fdb4c969f22689298404ed5
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394858B2

Notizen zur Reaktion

Wird geladen…