Formaldehyde → 1-(4-Methoxybenzyl)-4-hydroxyethyl-3-nitro-2-pyridone

HRID 1594661Notes

Reaction equation

HRID 1594661 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-:17])=[O:16])[C:9]2=[O:18])=[CH:5][CH:4]=1.[CH2:21]=[O:22].C[O-].[Na+]>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:21][OH:22])=[C:10]([N+:15]([O-:17])=[O:16])[C:9]2=[O:18])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10942334Sodium MethoxideHCID 110111821-(4-Methoxybenzyl)-4-methyl-3-nitro-2-pyridone

Product 1

HCID 541704571-(4-Methoxybenzyl)-4-hydroxyethyl-3-nitro-2-pyridoneYield 59.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 1-(4-methoxybenzyl)-4-methyl-3-nitro-2-pyridone (1.38 g, 5.0 mmol) and paraformaldehyde (0.152 g) in dimethylsulfoxide (8 mL) was added sodium methoxide (0.018 g). After 2 hours, the mixture was diluted with ethyl acetate and washed with water. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was dried, filtered and evaporated. The residual solid was triturated with chloroform/ethyl acetate (10 mL, 1/1) and 1-(4-methoxybenzyl)-4-hydroxyethyl-3-nitro-2-pyridone was collected by filtration (0.496 g). Fractionation of the supernatant over silica gel (chloroform/ethyl acetate to ethyl acetate/methanol 99/1) gave additional product (0.404 g) (total yield, 2.96 mmol, 59%).

Workup

  1. washwashed with water
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. customthe combined organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residual solid was triturated with chloroform/ethyl acetate (10 mL, 1/1) and 1-(4-methoxybenzyl)-4-hydroxyethyl-3-nitro-2-pyridone
  7. filtrationwas collected by filtration (0.496 g)

Sources & evidence

ORD record
ord-d75160faa5ea44cd81b8dc38b113a2c4
Source dataset
uspto-grants-2001_09
Patent number
US06284768B1

Reaction notes

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