3-Methyl-2-nitro-5-(prop-1-en-2-yl)pyridine → 5-Isopropyl-3-methylpyridin-2-amine

HRID 594112Notes

Reaction equation

HRID 594112 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-])=O)=[N:4][CH:5]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:7]=1>C(O)C.[Pd]>[CH:8]([C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([NH2:11])=[N:4][CH:5]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 1

HCID 898758843-Methyl-2-nitro-5-(prop-1-en-2-yl)pyridine

Product 1

HCID 235305935-Isopropyl-3-methylpyridin-2-amineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-methyl-2-nitro-5-(prop-1-en-2-yl)pyridine (221 mg, 1.24 mmol) was dissolved in ethanol (25 mL) and hydrogenated using a H-cube flow hydrogenator (settings: 20° C., 1 bar, 1 mL/min flow rate) and a 10% Pd/C CatCart (30 mm) as the catalyst. The collected solution was concentration in vacuo to give the title compound (177 mg, 95%). LCMS (2 min, formic) Rt 0.50 min, m/z (ES+) 151 (M+H).

Workup

  1. customa H-cube flow hydrogenator (settings: 20° C., 1 bar, 1 mL/min flow rate)
  2. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-80c532cd76904b7bb73d18857ee808d5
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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