(2-Chloro-6-isopropyl-3-nitro-pyridin-4-yl)-ethyl-amine → N4-ethyl-6-isopropyl-pyridine-3,4-diamine hydrochloride

HRID 895555Notes

Reaction equation

HRID 895555 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([NH:11][CH2:12][CH3:13])[CH:5]=[C:4]([CH:14]([CH3:16])[CH3:15])[N:3]=1>CO.[Pd]>[ClH:1].[CH2:12]([NH:11][C:6]1[CH:5]=[C:4]([CH:14]([CH3:16])[CH3:15])[N:3]=[CH:2][C:7]=1[NH2:8])[CH3:13]

Participants

4

Reactant 1

HCID 22379920(2-Chloro-6-isopropyl-3-nitro-pyridin-4-yl)-ethyl-amine

Product 1

HCID 86587612N4-ethyl-6-isopropyl-pyridine-3,4-diamine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2-chloro-6-isopropyl-3-nitro-pyridin-4-yl)-ethyl-amine (0.56 g, 2.30 mmol) in MeOH (20 mL) containing 10% Pd/c (˜50 mg) is stirred under and atmosphere of H2 for 3.5 h. The reaction mixture is then filtered through a pad of Celite using MeOH. The filtrate is concentrated in vacuo. Toluene is added to the residue and then removed in vacuo. This is repeated once more, yielding N4-ethyl-6-isopropyl-pyridine-3,4-diamine hydrochloride as a dark solid. 1H NMR (CD3OD, 400 MHz) δ 7.46 (s, 1H), 6.60 (s, 1H), 3.43 (q, J=7.4 Hz, 2H), 3.03 (sept, J=6.8 Hz, 1H), 1.35 (t, J=7.4 Hz, 3H), 1.33 (d, J=6.8 Hz, 6H) ppm.

Workup

  1. filtrationThe reaction mixture is then filtered through a pad of Celite
  2. concentrationThe filtrate is concentrated in vacuo
  3. additionToluene is added to the residue
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-36dceba304ef4c97af4a519adb5422c7
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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