Ethanol → HCID 18424197, compound

HRID 1282344Notes

Reaction equation

HRID 1282344 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]([CH2:13][CH3:14])[C:11]([CH2:15][C:16]#N)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-:20].[Na+].C(O)C.[OH2:25]>>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]([CH2:13][CH3:14])[C:11]([CH2:15][C:16]([OH:25])=[O:20])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 18424230HCID 18424230, compound

Product 1

HCID 18424197HCID 18424197, compound

Procedure

A suspension of 3.52 g. (0.013 mole) of 5-(p-chlorobenzoyl)-1-ethylpyrrole-2-acetonitrile in 26 ml. 1N sodium hydroxide and 50 ml. of ethanol is refluxed for six hours. The mixture is then diluted with water and cooled. A solid precipitates which is filtered off and set aside. The ethanol is evaporated from the filtrate in vacuo. The collected precipitate is added to the concentrated filtrate, and the mixture is extracted with chloroform. The aqueous phase is separated, acidified with dilute hydrochloric acid, and the resulting precipitate (A) is collected by filtration and dried. The chloroform phase is evaporated and the residue refluxed with 12 ml. of 1N sodium hydroxide and 24 ml. of ethanol for 6 hours. The ethanol is evaporated in vacuo, and the remaining solution is diluted with water and washed with chloroform. The aqueous solution is acidified with dilute hydrochloric acid and the precipitated solid (B) is collected and dried. The two samples of acidic material (A and B) are combined and recrystallized from aqueous isopropanol to give 5-(p-chlorobenzoyl)-1-ethylpyrrole-2-acetic acid as a white solid, m.p. 149-153° C. Analysis: Calcd. for C15H14ClNO3: C, 61.75;H, 4.83; N, 4.80%. Found: C, 61.78;H, 4.94; N, 4.96%.

Workup

  1. additionA suspension of 3.52 g
  2. temperaturecooled
  3. customA solid precipitates which
  4. filtrationis filtered off
  5. customThe ethanol is evaporated from the filtrate in vacuo
  6. additionThe collected precipitate is added to the concentrated filtrate
  7. extractionthe mixture is extracted with chloroform
  8. customThe aqueous phase is separated
  9. filtrationthe resulting precipitate (A) is collected by filtration
  10. customdried
  11. customThe chloroform phase is evaporated
  12. temperaturethe residue refluxed with 12 ml
  13. customThe ethanol is evaporated in vacuo
  14. additionthe remaining solution is diluted with water
  15. washwashed with chloroform
  16. customthe precipitated solid (B) is collected
  17. customdried
  18. customrecrystallized from aqueous isopropanol

Sources & evidence

ORD record
ord-7ad7372152e841f4ac691d39c82d227f
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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