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

HRID 2356862Notes

Reaction equation

HRID 2356862 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-4b76c88344134945aad655eb52bc6d43
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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