3-Amino-1-propanol → 4-(3-Hydroxypropylamino)-3-nitropyridine

HRID 22494

Reaction equation

HRID 22494 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].C(=O)([O-])O.[Na+]>C(O)C>[OH:5][CH2:4][CH2:3][CH2:2][NH:1][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 516892Sodium BicarbonateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 5923304-(3-Hydroxypropylamino)-3-nitropyridineYield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-1-propanol (4.5 g, 60.0 mmol) was added slowly to a mixture of 4-chloro-3-nitropyridine (8.0 g, 50.5 mmol) and sodium hydrogen carbonate (4.2 g, 50.0 mmol) in ethanol (200 ml). The mixture was stirred for 3 h at ambient temperature and the solvent removed under reduced pressure. Saturated aqueous sodium hydrogen carbonate (50 ml) was added to the residue, which was extracted with ethyl acetate (3×200 ml). The combined organics were dried over anhydrous sodium sulphate, filtered and evaporated. Crystallisation from ethyl acetate gave 4-(3-hydroxypropylamino)-3-nitropyridine (4.3 g, 43%) as an orange crystalline solid.

Workup

  1. customthe solvent removed under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate (50 ml) was added to the residue, which
  3. extractionwas extracted with ethyl acetate (3×200 ml)
  4. dry with materialThe combined organics were dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-cbf28fc31abd4ab98c1c3e2e3f42025f
Source dataset
uspto-grants-1995_06
Patent number
US05428168

Linked notes

Loading…