Hydroxyamine hydrochloride → N4,N4-Dipropylpyridine-2,4-diamine

HRID 2235488Notes

Reaction equation

HRID 2235488 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:14]=[C:13]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH:12]=[CH:11][N:10]=2)C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO>CO>[CH2:19]([N:15]([CH2:16][CH2:17][CH3:18])[C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[CH:14]=1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86049192HCID 86049192, compound

Product 1

HCID 86049193N4,N4-Dipropylpyridine-2,4-diamineYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.235 g (0.66 mmol) of N2-diphenylmethylene-N4,N4-dipropylpyridine-2,4-diamine in 9 mL of methanol was added 0.13 g (1.6 mmol) of sodium acetate followed by 0.082 g (1.2 mmol) of hydroxylamine hydrochloride. The resulting clear golden reaction mixture was stirred at room temperature for 45 min and concentrated in vacuo. The crude solids were slurried in dichloromethane, filtered and the filtrate was concentrated. The resulting oil was purified by flash chromatography eluting with a 13% to 20% methanol/dichloromethane gradient containing 2% triethylamine to give 0.106 g (83%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customThe resulting oil was purified by flash chromatography
  5. washeluting with a 13% to 20% methanol/dichloromethane gradient
  6. additioncontaining 2% triethylamine

Sources & evidence

ORD record
ord-906d03d15df641b59cebeab2c91fa840
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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