2-(Benzyloxy)-4-(2,4-dichlorophenyl)-3-nitropyridine → 4-(2,4-dichloro-phenyl)-3-nitro-1H-pyridin-2-one

HRID 1831505Notes

Reaction equation

HRID 1831505 reaction equation
C([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[C:13]1[CH:12]=[CH:11][NH:10][C:9](=[O:8])[C:14]=1[N+:15]([O-:17])=[O:16]

Participants

3

Reactant 1

HCID 220521282-(Benzyloxy)-4-(2,4-dichlorophenyl)-3-nitropyridine

Product 1

HCID 220520964-(2,4-dichloro-phenyl)-3-nitro-1H-pyridin-2-oneYield 23%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-Benzyloxy-4-(2,4-dichloro-phenyl)-3-nitro-pyridine (5.79 g, 15.4 mmol) was dissolved in TFA (20 mL) and stirred at room temperature for 4 h. The reaction mixture was concentrated and washed with 20% EtOAc/Hexane, and concentrated in vacuo to yield 1.0 g (23%) of 4-(2,4-dichloro-phenyl)-3-nitro-1H-pyridin-2-one as a solid: crude MS (AP) m/z 285.1 [(M+H)+, 100].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with 20% EtOAc/Hexane
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6767736011bb4d2ba9ce209c608b1032
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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