2-(4-tert-butyl-phenyl)-8-nitro-3,4-dihydro-2H-isoquinolin-1-one → 8-amino-2-(4-tert-butyl-phenyl)-3,4-dihydro-2H-isoquinolin-1-one

HRID 133112Notes

Reaction equation

HRID 133112 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[C:14]([N+:21]([O-])=O)[CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CCOC(C)=O>[NH2:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[C:12](=[O:24])[N:11]([C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)[CH2:20][CH2:19]2

Participants

4

Reactant 1

HCID 691594242-(4-tert-butyl-phenyl)-8-nitro-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 691593468-amino-2-(4-tert-butyl-phenyl)-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the nitro compound (Step D, 100 mg, 0.31 mmol) and EtOAc (5 mL) was hydrogenated over 10% Pd/C (20 mg) at atmospheric pressure and RT. After 3 h, the mixture was filtered through Celite® and concentrated in vacuo. Purification by silica flash chromatography (0-15% EtOAc:hexane) gave the desired compound as a white solid. MS m/e 295 (M+H)+. Calc'd for C19H22N2O-294.17.

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. customPurification by silica flash chromatography (0-15% EtOAc:hexane)

Sources & evidence

ORD record
ord-f1130cb546854d2aa6970e7f5f8a8462
Source dataset
uspto-grants-2008_06
Patent number
US07390820B2

Reaction notes

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