2-Benzyloxy-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-pyridine → 4-(2-chloro-4-difluoromethoxy-phenyl)3-nitro-3H-pyridin-2-one

HRID 1831549Notes

Reaction equation

HRID 1831549 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]([O:24][CH:25]([F:27])[F:26])=[CH:20][C:19]=2[Cl:28])[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:28][C:19]1[CH:20]=[C:21]([O:24][CH:25]([F:27])[F:26])[CH:22]=[CH:23][C:18]=1[C:13]1[CH:14]([N+:15]([O-:17])=[O:16])[C:9](=[O:8])[N:10]=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 220520472-Benzyloxy-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-pyridine

Product 1

HCID 220521384-(2-chloro-4-difluoromethoxy-phenyl)3-nitro-3H-pyridin-2-oneYield 19%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-Benzyloxy-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-pyridine(6.90 g, 17.0 mmol) was dissolved in TFA (25 mL) and stirred at room temperature for 4 h. The reaction mixture was concentrated in vacuo. Purification using flash chromatography (15% MeOH/DCM) gave 1.00 g (19%) of 4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-3H-pyridin-2-one as an orange solid: MS(AP) m/z 316.9 [(M+H)+, 98], 359.8 [(M+H+CH3CN)+, 100].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-71eea6fb480a4e9b8db46c7edaa4b7ac
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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