Ethyl Acetate → 4-Formyl-5-nitro-2-phenoxypyridine

HRID 491865Notes

Reaction equation

HRID 491865 reaction equation
CN(C)C=[CH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][N:8]=[C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=1.I([O-])(=O)(=O)=[O:23].[Na+].CCOC(C)=O>C1COCC1.O>[N+:11]([C:10]1[C:5]([CH:4]=[O:23])=[CH:6][C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH:9]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 86616325Dimethyl-[2-(5-nitro-2-phenoxy-pyridin-4-yl)-vinyl]-amine

Product 1

HCID 576783284-Formyl-5-nitro-2-phenoxypyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl-[2-(5-nitro-2-phenoxy-pyridin-4-yl)-vinyl]-amine (0.2 g, 0.7 mmol) in THF (2 mL) and water (2 mL) was added sodium periodate (0.46 g, 2.1 mmol). The reaction mixture was stirred for 30 min, treated with EtOAc and the solids filtered. The filtrate was washed with sat NaHCO3, dried (Na2SO4), and concentrated to yield 5-nitro-2-phenoxy-pyridine-4-carbaldehyde, the title compound, as a bright yellow solid.

Workup

  1. filtrationthe solids filtered
  2. washThe filtrate was washed with sat NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f0525406590643b490cf3b5057861afd
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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