Ammonia → HCID 67694201, compound

HRID 1455937Notes

Reaction equation

HRID 1455937 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13]([CH3:15])=O)[CH:2]=1.[NH3:17]>C(O)(C)C.Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][O:10][C:11]([C:12]2[CH:2]([CH2:3][CH2:4][CH3:5])[C:12]([C:11]([O:10][CH2:9][CH2:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:16])=[C:13]([CH3:15])[NH:17][C:13]=2[CH3:15])=[O:16])[CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 13605202HCID 13605202, compound

Product 1

HCID 67694201HCID 67694201, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

2.2 g of acetoacetic acid 3-(3-pyridyl)propyl ester and 0.36 g of n-butylaldehyde were heated and refluxed in the presence of 1 ml of concentrated ammonia solution in 20 ml of isopropanol for 7 hours. After the reaction, the reaction solution was condensed to dryness under reduced pressure, the residue was dissolved in 1N hydrochloric acid, washed with ethyl acetate, then made alkaline by sodium hydroxide and extracted by ethyl acetate. The extracted solution was rinsed, then dried over anhydrous sodium sulfate and condensed to dryness under reduced pressure, then the oily substance was refined by silica gel column chromatography to obtain the target compound in an amount of 1.24 g (51.9%).

Workup

  1. customAfter the reaction
  2. customcondensed to dryness under reduced pressure
  3. washwashed with ethyl acetate
  4. extractionextracted by ethyl acetate
  5. washThe extracted solution was rinsed
  6. dry with materialdried over anhydrous sodium sulfate and condensed to dryness under reduced pressure
  7. customto obtain the target compound in an amount of 1.24 g (51.9%)

Sources & evidence

ORD record
ord-5040d17683cb4240abfdc355e3eb6ebb
Source dataset
uspto-grants-1998_12
Patent number
US05843950

Reaction notes

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