Dimethylformamide dimethyl acetal → 4-(4-Methoxypyridin-2-yl)-2-nitrobenzaldehyde

HRID 1060003Notes

Reaction equation

HRID 1060003 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH:4]=1.C[O:20]C(OC)N(C)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:20])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 186310034-(4-Methoxypyridin-2-yl)-2-nitrotoluene

Product 1

HCID 186675454-(4-Methoxypyridin-2-yl)-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-(4-methoxypyridin-2-yl)-2-nitrotoluene (2.5 g) in N,N-dimethylformamide (15 ml) was added N,N-dimethylformamide dimethyl acetal (2.72 ml), and the mixture was stirred at 140° C. for 24 hours under a nitrogen atmosphere. The reaction mixture was evaporated under reduced pressure, and the residue was suspended in tetrahydrofuran (60 ml) and water (60 ml). Sodium metaperiodate (6.57 g) was added to the suspension, and the mixture was stirred at ambient temperature for 3 hours. The reaction mixture was filtered, and the filtrate was extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 150 g, 25-45% ethyl acetate in n-hexane) to give 4-(4-methoxypyridin-2-yl)-2-nitrobenzaldehyde (1.99 g).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionSodium metaperiodate (6.57 g) was added to the suspension
  3. stirringthe mixture was stirred at ambient temperature for 3 hours
  4. filtrationThe reaction mixture was filtered
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel 150 g, 25-45% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-f5c2a905307645d496bfa72357bead6e
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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