Nitromethane → 2-Methoxy-3-(2-nitroethenyl)-5-ethyl-6-methylpyridine

HRID 1033020Notes

Reaction equation

HRID 1033020 reaction equation
[CH3:1][O:2][C:3]1[N:10]=[C:9]([CH3:11])[C:8]([CH2:12][CH3:13])=[CH:7][C:4]=1[CH:5]=O.[N+:14]([CH3:17])([O-:16])=[O:15].Cl.CN.[OH-].[Na+]>C(O)C.CO>[CH3:1][O:2][C:3]1[C:4]([CH:5]=[CH:17][N+:14]([O-:16])=[O:15])=[CH:7][C:8]([CH2:12][CH3:13])=[C:9]([CH3:11])[N:10]=1

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 6364545Methylamine hydrochlorideHCID 102616792-Methoxy-5-ethyl-6-methylnicotinaldehyde

Product 1

HCID 541049542-Methoxy-3-(2-nitroethenyl)-5-ethyl-6-methylpyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-methoxy-5-ethyl-6-methylnicotinaldehyde (2.25 g, 12.6 mmol), nitromethane (1.9 g, 31.1 mmol), monomethylamine hydrochloride (69 mg) and sodium hydroxide (20 mg) in absolute ethanol (1.3 mL) was stirred at ambient temperature for three days. This mixture was diluted with methanol and the precipitated yellow crystalline product was collected by filtration to yield 2.39 g (86%), m.p. 105°-107° C.

Workup

  1. filtrationthe precipitated yellow crystalline product was collected by filtration
  2. customto yield 2.39 g (86%), m.p. 105°-107° C.

Sources & evidence

ORD record
ord-82781bfacc6b4987961c3f7bbaf07d2a
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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