2-Methoxy-3-(2-nitroethenyl)-5-ethyl-6-methylpyridine → 3-Pyridineethanamine,5-ethyl-2-methoxy-6-methyl-

HRID 1033021Notes

Reaction equation

HRID 1033021 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=[CH:10][N+:11]([O-])=O)=[CH:7][C:6]([CH2:14][CH3:15])=[C:5]([CH3:16])[N:4]=1>CO.Cl.[Pd]>[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][C:6]([CH2:14][CH3:15])=[C:5]([CH3:16])[N:4]=1

Participants

5

Reactant 1

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

Product 1

HCID 103977473-Pyridineethanamine,5-ethyl-2-methoxy-6-methyl-

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of 2-methoxy-3-(2-nitroethenyl)-5-ethyl-6-methylpyridine (445 mg, 2.0 mmol) in methanol (10 mL) and 4.7M methanolic hydrogen chloride (2 mL) containing 5% palladium/carbon (110 mg) was hydrogenated at atmospheric pressure over 10-20 hours. The catalyst was filtered off and the solvent evaporated. The residue was made basic with sodium hydroxide solution and the product extracted into methylene chloride, dried, filtered and the solvent evaporated to yield 332 mg of crude oily product. No further purification was performed.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. extractionthe product extracted into methylene chloride
  4. customdried
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customto yield 332 mg of crude oily product
  8. customNo further purification

Sources & evidence

ORD record
ord-237e1545cc224a6f89c90854faacd266
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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