Water → HCID 43811255, compound

HRID 348517Notes

Reaction equation

HRID 348517 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C([O-])(=O)C.[Na+].Cl.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27]N)=[CH:23][CH:22]=1.O>C(O)(=O)C>[CH2:11]([O:10][C:8]([CH:5]1[CH2:6][C:7]2[C:25]3[C:24](=[CH:23][CH:22]=[C:21]([O:20][CH3:19])[CH:26]=3)[NH:27][C:2]=2[CH2:3][CH2:4]1)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 517045Sodium AcetateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 43811255HCID 43811255, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ethyl 4-oxocyclohexanecarboxylate (3 g, 17.6 mmol) and sodium acetate (1.59 g, 19.4 mmol) in glacial acetic acid (36 mL) was degassed with nitrogen prior to addition of 4-methoxyphenylhydrazine hydrochloride (3.38 g, 19.4 mmol). The mixture was heated at reflux for 2 hours then cooled, poured into water and extracted with tert-butylmethyl ether. The organic phase was washed with 5% K2CO3, then water and finally brine. The organic layer was dried over sodium sulphate then solvent removed under reduced pressure and the residue purified by column chromatography to afford 3.29 g of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturethen cooled
  4. extractionextracted with tert-butylmethyl ether
  5. washThe organic phase was washed with 5% K2CO3
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customsolvent removed under reduced pressure
  8. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-89c1ccf7ba3543cf8ae8c2744b6254b8
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

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