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

HRID 1783692Notes

Reaction equation

HRID 1783692 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>CCOC(C)=O.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 EtOAc (40 ml) at RT. 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-31dcd2062b3b4bc9b735d00e5825c3f3
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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