2-methoxy-4-methyl-5-nitropyridine 4-Methyl-5-nitro-2-pyrrolidin-1-ylpyridine → 6-Methoxy-4-methylpyridin-3-amine

HRID 1628421Notes

Reaction equation

HRID 1628421 reaction equation
CC1C([N+]([O-])=O)=CN=C(N2CCCC2)C=1.[CH3:16][O:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([N+:25]([O-])=O)=[CH:20][N:19]=1>[Pd].O1CCCC1>[CH3:16][O:17][C:18]1[N:19]=[CH:20][C:21]([NH2:25])=[C:22]([CH3:24])[CH:23]=1

Participants

4

Reactant 1

HCID 866480992-methoxy-4-methyl-5-nitropyridine 4-Methyl-5-nitro-2-pyrrolidin-1-ylpyridine

Product 1

HCID 2431706-Methoxy-4-methylpyridin-3-amineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methoxy-4-methyl-5-nitropyridine 4-Methyl-5-nitro-2-pyrrolidin-1-ylpyridine (1.68 g, 10.0 mmol) and 10% palladium on carbon (168 mg) in tetrahydrofuran (10 mL) was stirred under hydrogen atmosphere at room temperature for 6 hr. Catalyst was removed by filtration and the filtrate was concentrated in vacuo to give the title compound (1.31 g, 9.49 mmol, 95%) as a pale brown solid.

Workup

  1. customCatalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1ba2e585c0424e5f8da684c992e65443
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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