Methanol → 2-[3-(2,6-dimethylphenyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 745491

Reaction equation

HRID 745491 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[CH:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].CO>C1COCC1.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22]

Participants

5

Reactant 2

HCID 887MethanolHCID 544475222-[3-(2,6-dimethylphenyl)-2-propenyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 136567382-[3-(2,6-dimethylphenyl)propyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound of Example 32 (10 g, 34 mmole) dissolved in 120 ml of THF and 100 ml of MeOH was reduced in a standard Parr hydrogenation apparatus using 1 g of 5% Pd/C as catalyst. The reaction was run at room temperature under a pressure of 5 psi for 24 hours. The residue after removing all solvent under reduced pressure was chromotographed to yield the pale yellow crystalline product which was recrystallized from Skelly B. The melting point was 92°-93.5° C.

Workup

  1. customThe residue after removing all solvent under reduced pressure
  2. customto yield the pale yellow crystalline product which
  3. customwas recrystallized from Skelly B

Sources & evidence

ORD record
ord-9db3a1f7933147b392b59faf3b177a1a
Source dataset
uspto-grants-1986_07
Patent number
US04599325

Linked notes

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