HCID 68509556, compound → methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochloride

HRID 1808328Notes

Reaction equation

HRID 1808328 reaction equation
[ClH:1].C([N:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=2)[CH2:10]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[ClH:1].[CH2:10]1[C:11]2[C:16](=[CH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)[CH2:17][NH:9]1

Participants

5

Reactant 2

HCID 68509556HCID 68509556, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19828495methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochlorideYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (4.3 g) was added to a solution of methyl 2-benzylisoindoline-5-carboxylate hydrochloride (43 g; 1 equiv.) in 800 ml of methanol. The mixture was hydrogenated for 90 minutes at 60 mm hydrogen. When the conversion was complete, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the crude product was recrystallised from chloroform. In this manner the desired product (25.39 g; 84%) was obtained in the form of a white solid having a purity of 98.63%.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe crude product was recrystallised from chloroform

Sources & evidence

ORD record
ord-b9fd1ca576e54be392ab915f3a13d6c0
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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