Sodium Hydroxide → HCID 20164602, compound

HRID 255860Notes

Reaction equation

HRID 255860 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][N:12]=[C:13]([C:19]([O:21]CC)=[O:20])[C:14]([O:16]CC)=[O:15])[CH3:4]>C(O)C>[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][N:12]=[C:13]([C:19]([OH:21])=[O:20])[C:14]([OH:16])=[O:15])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 85791371HCID 85791371, compound

Product 1

HCID 20164602HCID 20164602, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

48 ml of 2 N aqueous sodium hydroxide solution was added over 15 minutes to a stirred, refluxing mixture of 22.5 g of 53A in 48 ml of ethanol. A further 192 ml of 1 N aqueous sodium hydroxide solution was added over 20 minutes to the gently refluxing mixture. Then the mixture was filtered through Celite, and the filtrate was poured into a stirred mixture of 30 ml of concentrated hydrochloric acid, 90 ml of water and about 100 g of ice. The mixture was filtered. The solid was washed with water, dried under reduced pressure, and dissolved in methylene chloride. The solution was dried (MgSO4), filtered and stripped of solvent under reduced pressure. The residue was recrystallized from ethanol/water, and dissolved in methylene chloride. The solution was dried (MgSO4) and the solvent was evaporated to give ((2-ethylphenyl)hydrazono)malonic acid (53B), as a solid, m.p.: 135°-136° C. (with decomposition).

Workup

  1. temperaturerefluxing
  2. temperaturegently refluxing mixture
  3. filtrationThen the mixture was filtered through Celite
  4. additionthe filtrate was poured into a stirred mixture of 30 ml of concentrated hydrochloric acid, 90 ml of water and about 100 g of ice
  5. filtrationThe mixture was filtered
  6. washThe solid was washed with water
  7. customdried under reduced pressure
  8. dissolutiondissolved in methylene chloride
  9. dry with materialThe solution was dried (MgSO4)
  10. filtrationfiltered
  11. customThe residue was recrystallized from ethanol/water
  12. dissolutiondissolved in methylene chloride
  13. dry with materialThe solution was dried (MgSO4)
  14. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4d80c76a91c24d9bafb0107123fb6a9f
Source dataset
uspto-grants-1987_10
Patent number
US04699651

Reaction notes

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