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

HRID 508571Notes

Reaction equation

HRID 508571 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 19828495methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochlorideYield 2,242.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-29d8c84632db486f9946cff7b9c082d5
Source dataset
uspto-grants-2015_08
Patent number
US09096518B2

Reaction notes

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