4-Chlorobenzaldehyde → HCID 23004188, compound

HRID 322137Notes

Reaction equation

HRID 322137 reaction equation
O=[C:2]([CH2:11][CH2:12][CH3:13])[CH2:3][C:4]([O:6]CCC#N)=[O:5].[NH2:14]/[C:15](/[CH3:21])=[CH:16]\[C:17]([O:19][CH3:20])=[O:18].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1>C(O)(C)C>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([CH3:21])[NH:14][C:2]([CH2:11][CH2:12][CH3:13])=[C:3]2[C:4]([OH:6])=[O:5])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 23004047HCID 23004047, compound

Product 1

HCID 23004188HCID 23004188, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-cyanoethyl 3-oxohexanoate (11.9 mmol), methyl 3-aminocrotonate (11.9 mmol), and 4-chlorobenzaldehyde in 25 mL of isopropanol is heated at reflux temperature for 16 h, cooled, and the solvent is removed under reduced pressure. The residue is dissolved in 15 mL of dioxane and 626 mg of NaOH in 15 mL of water is added to the reaction mixture. After 0.5 hrs, the solution is concentrated to a small volume under reduced pressure, partitioned between 50 mL of water and 50 mL of ethyl acetate, separated, and the aqueous solution is washed with 2×20 mL of ethyl acetate. The organic solutions are discarded. The aqueous extract is acidified with concentrated HCl (pH=2), and the precipitated oil is extracted with ethyl acetate (2×40 mL). The combined organic extracts are dried (MgSO4), and the solvent is removed in vacuo to give a residue, which is characterized spectroscopically.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 16 h
  3. temperaturecooled
  4. customthe solvent is removed under reduced pressure
  5. dissolutionThe residue is dissolved in 15 mL of dioxane
  6. addition626 mg of NaOH in 15 mL of water is added to the reaction mixture
  7. concentrationthe solution is concentrated to a small volume under reduced pressure
  8. custompartitioned between 50 mL of water and 50 mL of ethyl acetate
  9. customseparated
  10. washthe aqueous solution is washed with 2×20 mL of ethyl acetate
  11. extractionThe aqueous extract
  12. extractionthe precipitated oil is extracted with ethyl acetate (2×40 mL)
  13. dry with materialThe combined organic extracts are dried (MgSO4)
  14. customthe solvent is removed in vacuo
  15. customto give a residue, which

Sources & evidence

ORD record
ord-7b198dc8488244298ca4d46d3a78c266
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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