2-Nitrobenzaldehyde → HCID 13560825, compound

HRID 2309185Notes

Reaction equation

HRID 2309185 reaction equation
[NH2:1]/[C:2](/[CH3:9])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:10]([CH:12]([C:16](=O)[CH2:17][O:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[C:13]([OH:15])=[O:14])[CH3:11].[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34]C=1C=O)([O-:29])=[O:28].[C:38](O)(=O)/[CH:39]=C\C(O)=O>C(O)C.C(OCC)(=O)C>[CH2:7]([O:6][C:4]([C:3]1[CH:10]([C:11]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[N+:27]([O-:29])=[O:28])[C:12]([C:13]([O:15][CH2:38][CH3:39])=[O:14])=[C:16]([CH2:17][O:18][CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[NH:1][C:2]=1[CH3:9])=[O:5])[CH3:8]

Participants

7

Reactant 4

HCID 111012-NitrobenzaldehydeHCID 444266Maleic AcidHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 19866608HCID 19866608, compound

Product 1

HCID 13560825HCID 13560825, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 3-aminocrotonate (1.3g, 0.01 mol), ethyl 3-oxo-4-(3-pyridylmethoxy) butanoic acid (2.4 g 0.01 mol) and 2-nitrobenzaldehyde (1.56g, 0.01 m) in ethanol (50 ml) was refluxed for 23 hours. The solvent was removed under reduced pressure and the residue treated with diethyl ether and extracted with 2N hydrochloric acid. The separated aqueous phase was extracted with chloroform and the chloroform phase separated and evaporated. The residue was treated with acetone and left overnight. Solid material which separated was filtered off and discarded. The acetone solution was evaporated, treated with ammonia solution and extracted with chloroform (×3). The combined chloroform extracts were washed with water, dried (MgSO4) and evaporated to give an oil. This was dissolved in ethyl acetate and treated with maleic acid (1 g). A little of the solvent was evaporated and acetone and diethyl ether added. The maleic salt of the title compound crystallised and was collected (2.6 g) mp 133-135° C.

Workup

  1. temperaturewas refluxed for 23 hours
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue treated with diethyl ether
  4. extractionextracted with 2N hydrochloric acid
  5. extractionThe separated aqueous phase was extracted with chloroform
  6. customthe chloroform phase separated
  7. customevaporated
  8. additionThe residue was treated with acetone
  9. customSolid material which separated
  10. filtrationwas filtered off
  11. customThe acetone solution was evaporated
  12. additiontreated with ammonia solution
  13. extractionextracted with chloroform (×3)
  14. washThe combined chloroform extracts were washed with water
  15. dry with materialdried (MgSO4)
  16. customevaporated
  17. customto give an oil
  18. customA little of the solvent was evaporated
  19. additionacetone and diethyl ether added
  20. customThe maleic salt of the title compound crystallised
  21. customwas collected (2.6 g) mp 133-135° C.

Sources & evidence

ORD record
ord-2eb3ac910bec419ba0c4a61c76a00946
Source dataset
uspto-grants-1987_09
Patent number
US04694012

Reaction notes

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