Acetic Acid → HCID 86737803, compound

HRID 1680479Notes

Reaction equation

HRID 1680479 reaction equation
C(CC[C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)#N.[OH-].[K+].C(O)(=[O:24])C.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>C(O)C.CCOCC>[OH2:24].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[C:29]([CH2:28][CH2:27][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]([CH2:14][C:15]2[NH:19][CH:18]=[CH:17][N:16]=2)=[CH:5]1)([OH:31])=[O:30]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 444972Fumaric AcidHCID 86737804HCID 86737804, compound

Product 1

HCID 86737803HCID 86737803, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(2-cyanoethyl-3-(1-imidazolyl methyl)-indole (1.0 g) and 10% aqueous potassium hydroxide (10 ml) was heated under reflux for 2 hours to give a clear solution. The solution was just acidified with acetic acid and then evaporated. The residue was chromatographed on silica gel. Elution with a mixture of chloroform and methanol (1:1) gave first a small amount of impurity followed by pure product. Evaporation of the product-containing eluate gave an oil which was dissolved in the minimum volume of ethanol. A slight excess of a saturated ethanolic solution of fumaric acid was added and the mixture was diluted with ether. The precipitate was collected by filtration and crystallised from methanol to give 1-(2-carboxyethyl)-3-(1-imidazolylmethyl)indole fumarate monohydrate 0.45 g, m.p. 161°-163° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customto give a clear solution
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washElution
  7. additionwith a mixture of chloroform and methanol (1:1)
  8. customgave first a small amount of impurity
  9. customEvaporation of the product-containing eluate
  10. customgave an oil which
  11. filtrationThe precipitate was collected by filtration
  12. customcrystallised from methanol

Sources & evidence

ORD record
ord-6748e35728b34ccaa913f248127579cf
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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