Pyridine → 5-nitro-1-phenyl-1H-pyridin-2-one

HRID 2375894Notes

Reaction equation

HRID 2375894 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[N+:8]([C:5]1[CH:6]=[CH:7][C:2](=[O:1])[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 178526703HCID 178526703, compound

Product 1

HCID 223189695-nitro-1-phenyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[Ref. Mederski, W. W. K. R., et al. Tetrahedron, 1999, 55, 12757-12770.] To a solution of 2-hydroxy-5-nitropyridine (1.07 g, 7.64 mmol) in dry methylene chloride (50 mL) were added phenylboronic acid (1.86 g, 15.3 mmol), cupric acetate (1.71 g, 9.41 mmol), pyridine (1.2 mL, 15.3 mmol), triethylamine (2.1 mL, 15.3 mmol) and activated 4 Å molecular sieves (2 g). The resulting mixture was stirred in air at rt for 2 d. The mixture was then filtered through celite and washed with methylene chloride. The crude material was purified by silica gel chromatography, eluting with CH2Cl2:EtOAc (85:15) to give the title compound as a white solid. LC-MS (ES, Pos.): 217 [MH+], and 1H NMR (CDCl3, 400 MHz): δ=6.67 (d, J=10.1 Hz, 1H), 7.39-7.42 (m, 2H), 7.53-7.58 (m, 3H), 8.17 (dd, J=10.1, 3.1 Hz, 1H), 8.67 (d, J=3.1 Hz, 1H).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashed with methylene chloride
  3. customThe crude material was purified by silica gel chromatography
  4. washeluting with CH2Cl2:EtOAc (85:15)

Sources & evidence

ORD record
ord-5df8e1e3239148efabaeb3a58f21b401
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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