HCID 68828481, compound → HCID 16772620, compound

HRID 450093Notes

Reaction equation

HRID 450093 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[CH2:14]([N:10]([CH2:11][CH2:12][CH3:13])[C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][N:8]=1)[CH2:15][CH3:16]

Participants

4

Reactant 1

HCID 68828481HCID 68828481, compound

Product 1

HCID 16772620HCID 16772620, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (5-nitro-pyridin-2-yl)-dipropylamine (630 mg, 2.82 mmol) in methanol (10 ml) was hydrogenated over 10% Pd—C (130 mg) at room temperature and atmospheric pressure until no further gas absorption occurred. The reaction mixture was filtered over celite and the filtrate was concentrated to an oil. Purification by column chromatography over silica gel using 0-20% ethyl acetate in pet ether yielded N2,N2-dipropyl-pyridine-2,5-diamine (336 mg, 46.5%) as oil.

Workup

  1. customatmospheric pressure until no further gas absorption
  2. filtrationThe reaction mixture was filtered over celite
  3. concentrationthe filtrate was concentrated to an oil
  4. customPurification by column chromatography over silica gel using 0-20% ethyl acetate in pet ether

Sources & evidence

ORD record
ord-63fd44e121c44962ad5ed6ebd2977b8d
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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