4-Bromo-2-(4-nitro-phenyl)-2H-phthalazin-1-one → 2-(4-amino-phenyl)-4-bromo-2H-phthalazin-1-one

HRID 1765378Notes

Reaction equation

HRID 1765378 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[N:3]=1>C(OCC)(=O)C.O=[Pt]=O>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([N:4]2[N:3]=[C:2]([Br:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:12])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 211065554-Bromo-2-(4-nitro-phenyl)-2H-phthalazin-1-one

Product 1

HCID 211065172-(4-amino-phenyl)-4-bromo-2H-phthalazin-1-oneYield 67%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-2-(4-nitro-phenyl)-2H-phthalazin-1-one (see Method B) (1.0 g, 2.9 mmol) and PtO2 (0.13 g, 0.58 mmol) were dissolved in ethyl acetate (40 ml) at room temperature. The mixture was hydrogenated at ambient pressure for 2 h, before the catalyst was filtered off to yield title compound (0.61 g, 67% yield). 1H-NMR: (400 MHz, D6-DMSO) 8.34 (1H, d), 8.07 (1H, t), 7.99 (2H, t), 7.18 (2H, d), 6.63 (2H, d), 5.35 (2H, s); MS (ESI+)=318.42 (M+H)+.

Workup

  1. filtrationwas filtered off

Sources & evidence

ORD record
ord-1144b9ec3e5445b7ab5ad33d7ef18997
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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