Potassium Hydroxide → p-(2-Thenoyl)hydratropohydroxamic acid

HRID 461726Notes

Reaction equation

HRID 461726 reaction equation
[C:1]1([C:6]([C:8]2[CH:20]=[CH:19][C:11]([CH:12]([CH3:18])[C:13](OCC)=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH:22][NH2:23].[OH-].[K+]>CO>[C:1]1([C:6]([C:8]2[CH:20]=[CH:19][C:11]([CH:12]([CH3:18])[C:13]([NH:23][OH:22])=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 12232951Ethyl p-(2-thenoyl)hydratropate

Product 1

HCID 12232963p-(2-Thenoyl)hydratropohydroxamic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a stirred solution of 12.6 parts of ethyl p-(2-thenoyl)-hydratropate in 35 parts of methanol is added successively and while cooling, first a solution of 6.05 parts of hydroxyl amine hydrochloride in 35 parts of methanol and then a solution of 7.3 parts of potassium hydroxide in 35 parts of methanol. Upon completion, the whole is stirred for 30 minutes. The mixture is filtered and the filtrate is stirred for 3 days at room temperature. The reaction mixture is evaporated and the residue is taken up in water. The aqueous solution is acidified with hydrochloric acid solution and the product is extracted with ether. The extract is washed with water, dried, filtered and evaporated. The residue is taken up in water, alkalized with sodium hydroxide solution, washed with ether and the aqueous phase is acidified with concentrated hydrochloric acid solution. The product is extracted with ether. The latter is washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silicagel, using a mixture of chloroform and 10% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is triturated in a mixture of petroleumether and diisopropylether. The solid product is filtered off and crystallized from 2-propanol, yielding p-(2-thenoyl)hydratropohydroxamic acid; m.p. 143.5° C.

Workup

  1. temperaturewhile cooling
  2. filtrationThe mixture is filtered
  3. stirringthe filtrate is stirred for 3 days at room temperature
  4. customThe reaction mixture is evaporated
  5. extractionthe product is extracted with ether
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. washwashed with ether
  11. extractionThe product is extracted with ether
  12. washThe latter is washed with water
  13. customdried
  14. filtrationfiltered
  15. customevaporated
  16. customThe residue is purified by column-chromatography over silicagel
  17. additiona mixture of chloroform and 10% of methanol as eluent
  18. customThe pure fractions are collected
  19. customthe eluent is evaporated
  20. customThe residue is triturated in a mixture of petroleumether and diisopropylether
  21. filtrationThe solid product is filtered off
  22. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-a325fa3b0edc419a90391618b03cea22
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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