HCID 178515085, compound → HCID 178507381, compound

HRID 585518Notes

Reaction equation

HRID 585518 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][SiH3:22])[CH:16]=1)[C:8]2=[O:13])([O-])=O>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][SiH3:22])[CH:16]=1)[C:8]2=[O:13]

Participants

4

Reactant 1

HCID 178515085HCID 178515085, compound

Product 1

HCID 178507381HCID 178507381, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitro-2-[3-(silylmethyl)benzyl]-1-isoindolinone (5.2 g, 12.5 mmol) in tetrahydrofuran (60 ml) is, in the presence of palladium (10% on carbon, 375 mg), stirred under an atmosphere of hydrogen for 20 h and filtered, and the filtrate is concentrated under reduced pressure. The desired product is purified by flash chromatography (cyclohexane/ethyl acetate mixtures). Yield: 3.8 g, 79% of theory.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe desired product is purified by flash chromatography (cyclohexane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-48304be940004e00ab06025895da0a82
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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