Acetic Acid → HCID 178418660, compound

HRID 465922Notes

Reaction equation

HRID 465922 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11].[CH:14]([C:16]1[N:17]=[CH:18][NH:19][CH:20]=1)=O.[BH4-].[Na+].C(O)(=O)C>CO.C(Cl)(Cl)Cl>[NH:19]1[CH:20]=[C:16]([CH2:14][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[N:17]=[CH:18]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 764281H-Imidazole-4-carbaldehydeHCID 4311764Sodium borohydride3×HCID 11240788HCID 11240788, compound

Product 1

HCID 178418660HCID 178418660, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of methyl (E)-3-(2-aminophenyl)propenoate (531.6 mg) and 4-formylimidazole (317.1 mg) in methanol (7.0 ml) was stirred at ambient temperature for 18 hours. To the reaction mixture was added sodium borohydride (56.5 mg) under stirring and cooling in an ice-bath. After the mixture was stirred for 2 hours at ambient temperature, sodium borohydride (56.5 mg) was added thereto. The mixture was stirred for 2 hours at ambient temperature. To the reaction mixture was added acetic acid in order to decompose the excess sodium borohydride and the methanol was removed under reduced pressure. To the residue were added diluted hydrochloric acid and ethyl acetate under stirring. The separated aqueous layer was basified with aqueous sodium bicarbonate and extracted twice with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated to give a residue, which was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and methanol (20:1) to afford pure methyl (E)-3-[2-(4-imidazolylmethylamino)phenyl]propenoate (0.7 g) as an oil.

Workup

  1. temperaturecooling in an ice-bath
  2. stirringAfter the mixture was stirred for 2 hours at ambient temperature
  3. stirringThe mixture was stirred for 2 hours at ambient temperature
  4. customthe methanol was removed under reduced pressure
  5. additionTo the residue were added diluted hydrochloric acid and ethyl acetate
  6. stirringunder stirring
  7. extractionextracted twice with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated
  11. customto give a residue, which

Sources & evidence

ORD record
ord-43678e1aaa9a4d789e9c75f96d7c1c8c
Source dataset
uspto-grants-1992_10
Patent number
US05155101

Reaction notes

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