Hydrochloric Acid → HCID 22101533, compound

HRID 1457959Notes

Reaction equation

HRID 1457959 reaction equation
CON=[C:4]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH:8]([O:13][CH3:14])[CH:7]([N:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)C(=O)C)[CH:6]=[C:5]1[CH3:26].C(O)(=O)C(C)=[O:29].Cl>C(O)C>[CH2:19]([NH:15][CH:7]1[CH:8]([O:13][CH3:14])[C:9]([CH3:12])([CH3:11])[CH2:10][C:4](=[O:29])[C:5]([CH3:26])=[CH:6]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1060Pyruvic AcidHCID 54284412HCID 54284412, compound

Product 1

HCID 22101533HCID 22101533, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethanol (40 ml) containing the 4-(N-acetylbenzylamino)-5-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one methyloxime obtained in step 3 (8.5 g, 23.7 millimoles) there were added pyruvic acid (4.18 g, 47.4 millimoles) and 6N hydrochloric acid (40 ml), and the mixture was heated at 75° C. for 4 hours. The reaction solution was concentrated and the resulting residue was dissolved in methanol (50 ml) and then neutralized with a 10% aqueous sodium hydroxide solution while stirring on ice. Water (100 ml) was added, extraction was performed with benzene, and after washing the benzene solution with water it was dried over anhydrous magnesium sulfate. The benzene was distilled off and the resulting residue was subjected to silica gel column chromatography with benzene-ethyl acetate (19:1) as the eluent, to obtain 4.72 g (69%) of 4-benzylamino-5-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one as a colorless oil.

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe resulting residue was dissolved in methanol (50 ml)
  3. additionWater (100 ml) was added
  4. extractionextraction
  5. washafter washing the benzene solution with water it
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationThe benzene was distilled off

Sources & evidence

ORD record
ord-1445dd69d138479dbddc9f5b56dd1f91
Source dataset
uspto-grants-1998_12
Patent number
US05849801

Reaction notes

Loading…