Diethyl Ether → HCID 16768062, compound

HRID 1058945Notes

Reaction equation

HRID 1058945 reaction equation
C(N(CC)CC)C.O=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].Cl.[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30]N)=[CH:26][CH:25]=1.CCOCC>C(O)C>[CH3:23][C:24]1[CH:25]=[C:26]2[C:27](=[CH:28][CH:29]=1)[NH:30][C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:10]2[CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 73914delta-Oxobenzenepentanoic acid

Product 1

HCID 16768062HCID 16768062, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (1.4 mL, 10 mmol) was added to a stirred suspension of δ-oxobenzenepentanoic acid (1.92 g, 10 mmol) and (4-methylphenyl)hydrazine hydrochloride (1.59 g, 10 mmol) in ethanol (16 mL) and the mixture was stirred at room temperature for 4 h. Ether (100 mL) was added, the mixture was filtered and the solvent was evaporated under reduced pressure. The residue was added slowly to trifluoroacetic acid (15 mL) and the mixture was heated under reflux for 2 h. The mixture was cooled, water (100 mL) was added and the mixture was extracted with ethyl acetate (100 mL). The organic fraction was washed with brine (30 mL), dried (MgSO4) and the volume was reduced to Ca. 10 mL by evaporation under reduced pressure. The precipitate was collected and recrystallized from ether to give the title compound as a pale solid (1.51 g, 54%). 1H NMR (360 MHz, DMSO-d6) δ2.39 (3H, s), 2.50-2.58 (2H, m), 3.03-3.09 (2H, m), 6.91-6.95 (1H, m), 7.23-7.25 (1H, m), 7.34-7.40 (2H, m), 7.47-7.63 (4H, m), 11.4 (1H, br s), and 12.25 (1H, br s). m/z (ES+) 280 (M+1).

Workup

  1. filtrationthe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was added slowly to trifluoroacetic acid (15 mL)
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 2 h
  6. temperatureThe mixture was cooled
  7. additionwater (100 mL) was added
  8. extractionthe mixture was extracted with ethyl acetate (100 mL)
  9. washThe organic fraction was washed with brine (30 mL)
  10. dry with materialdried (MgSO4)
  11. custom10 mL by evaporation under reduced pressure
  12. customThe precipitate was collected
  13. customrecrystallized from ether

Sources & evidence

ORD record
ord-8b76c828db4c49e08800ca2ad5783dfd
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

Loading…