4-Amino-1-butanol → HCID 19864513, compound

HRID 1199990Notes

Reaction equation

HRID 1199990 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C([O-])(O)=O.[Na+].[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]>C(O)C>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 258684-Amino-1-butanolHCID 516892Sodium BicarbonateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 19864513HCID 19864513, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-chloro-3-nitropyridine (8 g) and NaHCO3 (4.2 g) in ethanol (200 cm3) at room temperature was added over 3 minutes 4-aminobutanol (4.5 g). The mixture was stirred at room temperature for 11/4 hours and the solvent was then removed under vacuum. The residue was suspended in saturated aqueous NaHCO3 solution (50 ml) and extracted with ethyl acetate (3×250 ml). The combined organic extracts were dried over Na2SO4, filtered and evaporated. The residue was then recrystallised from ethyl acetate to afford the title compound, (6.5 g, 62%), as yellow crystals, m.p. 80-82°.

Workup

  1. customthe solvent was then removed under vacuum
  2. extractionextracted with ethyl acetate (3×250 ml)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was then recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-6ca1a17cb03e404ab717a3e13a727323
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

Loading…