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

HRID 1944722Notes

Reaction equation

HRID 1944722 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-c772fef17fdb4c969f22689298404ed5
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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