HCID 19363269, compound → HCID 19363234, compound

HRID 850506Notes

Reaction equation

HRID 850506 reaction equation
[CH2:1]([O:6][C:7]1[C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][N:10]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=1)[C:11]2=[O:22])[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>C(O)C.[C].[Pd]>[NH2:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][N:10]2[CH2:9][C:8]3[C:12](=[CH:13][CH:14]=[C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:7]=3[O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:11]2=[O:22])=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 19363269HCID 19363269, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363234HCID 19363234, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

4,5-Dipentyloxy-2-[2-(4-nitrophenyl)ethyl]-2,3-dihydroisoindol-1-one (19.69 g, 43.3 mmol, 1.0 eq) obtained in Example 7-30 was dissolved in ethanol (200 ml), and 5% palladium-carbon catalyst (3.8 g, water content 50%) was added. The reaction mixture was stirred in a stream of hydrogen at room temperature for 2.5 hours under the pressure of 3 kgf/cm2, and filtered through celite. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (ethyl acetate/chloroform=1/2) to give 2-[2-(4-aminophenyl)ethyl]-4,5-bispentyloxy-2,3-dihydroisoindol-1-one (17.19 g, 93.5%) as pale-yellow crystals.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by column chromatography on silica gel (ethyl acetate/chloroform=1/2)

Sources & evidence

ORD record
ord-066b3c5f20544d48bbad14aa119c7eb6
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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