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

HRID 547678Notes

Reaction equation

HRID 547678 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-fb3ff16ca5aa47d8aaf202afc4195519
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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