Ammonia → 3-Nitro-1-phenyl-1,2-dihydropyridin-2-one

HRID 497809Notes

Reaction equation

HRID 497809 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.N>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O1CCCC1.N1C=CC=CC=1>[N+:8]([C:7]1[C:2](=[O:1])[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 178526677HCID 178526677, compound

Product 1

HCID 223191573-Nitro-1-phenyl-1,2-dihydropyridin-2-oneYield 61%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

5 g of 2-hydroxy-3-nitropyridine, 7.14 g of phenylboronic acid, 2.6 g of copper(II) acetate, 9.9 ml of triethylamine and 5.8 ml of pyridine were added to 100 ml of tetrahydrofuran, followed by stirring overnight. The reaction mixture was poured into aqueous ammonia, and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated. The residue was suspended into ether, and collected by filtration, to give 4.71 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-58f3150fa2c940b1840b2c8bb39e0256
Source dataset
uspto-grants-2005_09
Patent number
US06949571B2

Reaction notes

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