Ethanol → HCID 14989647, compound

HRID 1199672Notes

Reaction equation

HRID 1199672 reaction equation
O.NN.[N+:4]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[N:11][CH:12]=1)([O-])=O.[CH2:19](O)C>[Pd]>[NH2:4][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 24654Hydrazine hydrate (1:1)HCID 14989637HCID 14989637, compound

Product 1

HCID 14989647HCID 14989647, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Hydrazine hydrate (10 ml) in ethanol (20 ml) was added over 30 minutes to a stirred suspension of 4-(5-nitropyrid-2-yl)butanoic acid (7.5 g, 0.036 mole) and 10% palladium on carbon (1 g) in ethanol (100 ml). The solution was stirred for 1 hour, filtered through hyflo and the filtrate was evaporated to dryness. The residue was dissolved in methanol (250 ml) containing concentrated sulphuric acid (20 ml) and the resulting solution was refluxed for 4 hours, cooled and the solvent was removed under reduced pressure. The residue was dissolved in water (100 ml), basified and extracted with chloroform (3×100 ml). The chloroform extracts were combined, dried over magnesium sulphate, and evaporated to dryness. The residue was distilled in a kugelrohr apparatus (oven temp. 145° C. at 0.05 mmHg) to give the title compound 3.84 g as a straw coloured oil.

Workup

  1. filtrationfiltered through hyflo
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in methanol (250 ml)
  4. additioncontaining concentrated sulphuric acid (20 ml)
  5. temperaturethe resulting solution was refluxed for 4 hours
  6. temperaturecooled
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in water (100 ml)
  9. extractionextracted with chloroform (3×100 ml)
  10. dry with materialdried over magnesium sulphate
  11. customevaporated to dryness
  12. distillationThe residue was distilled in a kugelrohr apparatus (oven temp. 145° C. at 0.05 mmHg)

Sources & evidence

ORD record
ord-7d4d345dcc82494aa53c2502810784c1
Source dataset
uspto-grants-1990_02
Patent number
US04902698

Reaction notes

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