Dimethylformamide dimethyl acetal → HCID 86616324, compound

HRID 491862Notes

Reaction equation

HRID 491862 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][N:9]=1.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([CH:14]=[CH:20][N:21]([CH3:23])[CH3:22])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 46313035HCID 46313035, compound

Product 1

HCID 86616324HCID 86616324, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2-(2-fluoro-phenyl)-4-methyl-5-nitro-pyridine (5.4 g, 23 mmol) in DMF (30 mL) was treated with N,N-dimethylformamide dimethyl acetal (3.6 g, 30 mmol), and the mixture was stirred at 115° C. for 1 h, cooled, and concentrated in vacuo to yield crude {2-[2-(2-fluoro-phenyl)-5-nitro-pyridin-4-yl]-vinyl}-dimethyl-amine as a brown solid. The solid was dissolved in THF (100 mL), and water (100 mL), and then sodium periodate (14.06 g, 66 mmol) was added. The suspension was stirred at room temperature for 24 h. The reaction mixture was filtered, and the filtrate was concentrated, and then diluted with EtOAc. The organic extract washed with saturated aqueous NaHCO3 solution, dried (Na2SO4), and concentrated in vacuo to yield crude title compound as a solid. The crude solid was purified by column chromatography (4:2:0.5; CHCl3:hexanes:EtOAc) to yield 2-(2-fluoro-phenyl)-5-nitro-pyridine-4-carbaldehyde, the title compound as a yellow solid.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8efcd9a5c3164000a391aa52e290ae6d
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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