1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-3-nitro-1H-pyridin-2-one → 3-amino-1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-1H-pyridin-2-one

HRID 2054588Notes

Reaction equation

HRID 2054588 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]4[O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:24]=4[CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:11]=[C:10]([N+:33]([O-])=O)[C:9]1=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.CN(C=O)C.O.C(OCC)(=O)C.[Pd]>[NH2:33][C:10]1[C:9](=[O:36])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]4[O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:24]=4[CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:11]=1

Participants

7

Reactant 1

HCID 596559561-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-3-nitro-1H-pyridin-2-one

Product 1

HCID 596559843-amino-1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-1H-pyridin-2-one

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-3-nitro-1H-pyridin-2-one (100 mg, 0.212 mmol) was dissolved in hot 50% ethanol in DMF (8 mL) and cooled to room temperature. 10% Pd—C (10 mg) was added and the solution was shaken on a Parr hydrogenator with 60 psi H2 for 2 h. The resulting mixture was diluted with water (30 mL) and ethyl acetate (70 mL), separated and extracted with ethyl acetate (100 mL). The combined organic layers were washed with sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 3-amino-1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-1H-pyridin-2-one as a yellow sold that was used without further purification.

Workup

  1. customseparated
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe combined organic layers were washed with sat'd aq NaCl
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e180ec040ee4738884b0384ad114356
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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