Putrescine → HCID 19864520, compound

HRID 1200001Notes

Reaction equation

HRID 1200001 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].C(OCC)(=O)C>C(O)C>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 1045PutrescineHCID 8857Ethyl AcetateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 19864520HCID 19864520, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1,4-diaminobutane (8.8 g) in ethanol (100 ml) at room temperature was added a solution of 4-chloro-3-nitropyridine in ethanol (50 ml). The mixture was stirred at room temperature for 30 minutes, poured into ethyl acetate (400 ml), and then washed with water (3×150 ml). The aqueous phases were back-extracted with methylene chloride (3×120 ml) and all the organic phases were combined, dried over Na2SO4, filtered and evaporated under vacuum. The residue was chromatographed on silica eluting with a mixture of methylene chloride and methanol containing 1% ammonium hydroxide. The fractions containing the product were combined and evaporated under vacuum to give the title compound, (4.2 g), which was used directly in the next step.

Workup

  1. washwashed with water (3×150 ml)
  2. extractionThe aqueous phases were back-extracted with methylene chloride (3×120 ml) and all the organic phases
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue was chromatographed on silica eluting with a mixture of methylene chloride and methanol containing 1% ammonium hydroxide
  7. additionThe fractions containing the product
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-2edd9f1a6cf84295bd76af664d581272
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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