2-(4-tert-butyl-phenyl)-8-nitro-2H-phthalazin-1-one → 8-amino-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one

HRID 133105Notes

Reaction equation

HRID 133105 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[N:20]=[CH: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:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=1)[N:20]=[CH:19]2

Participants

4

Reactant 1

HCID 691588672-(4-tert-butyl-phenyl)-8-nitro-2H-phthalazin-1-one

Product 1

HCID 691606278-amino-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the nitro compound (Step D) and EtOAc (10 mL) was hydrogenated over 10% Pd/C (20 mg) at RT and at atmospheric pressure. After 4 h, the mixture was filtered through Celite® and concentrated in vacuo to afford the desired compound as an orange oil. MS m/e 294 (M+H)+. Calc'd for C18H19N3O: 293.15.

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e0bf932c1e44e1e82edcbe72ba6a7d8
Source dataset
uspto-grants-2008_06
Patent number
US07390820B2

Reaction notes

Loading…