Hydrochloric Acid → HCID 22408484, compound

HRID 439868Notes

Reaction equation

HRID 439868 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7](C)[C:6]([O:10][CH3:11])=[C:5]([CH3:12])[C:4]=1[CH3:13])N.[CH3:14][CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=O.Cl.[CH2:26](O)C>>[CH3:13][C:4]1[C:3]2[N:1]=[C:16]3[C:17]4[C:22]([CH2:23][C:15]3([CH3:26])[C:14]=2[C:7]([CH3:8])=[C:6]([O:10][CH3:11])[C:5]=1[CH3:12])=[CH:21][CH:20]=[CH:19][CH:18]=4

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2492622-MethylindanoneHCID 22408464HCID 22408464, compound

Product 1

HCID 22408484HCID 22408484, compound

Procedure

A mixture of 2.2 g (0.012 mol) of 4-hydrazino-2,3,6trimethylanisole, 1.9 g (0.013 mol) of 2-methyl-1-indanone and 2 ml of conc. aqueous HCl in 20 ml of ethanol was refluxed under argon for 1 hour. After cooling the solvent was removed by evaporation and the residue was partitioned in a mixture of water and methylene chloride. The aqueous phase was neutralized by addition of aqueous NaHCO3 and the phases separated. After drying (MgSO4) and evaporation of the organic phase, the remaining crude product was purified by chromatography on silica using methylene chloride as an eluant. This gave 1.1 g 31% of the product which was used directly in the next step.

Workup

  1. temperaturewas refluxed under argon for 1 hour
  2. temperatureAfter cooling the solvent
  3. customwas removed by evaporation
  4. customthe residue was partitioned in a mixture of water and methylene chloride
  5. additionThe aqueous phase was neutralized by addition of aqueous NaHCO3
  6. customthe phases separated
  7. customAfter drying
  8. custom(MgSO4) and evaporation of the organic phase
  9. customthe remaining crude product was purified by chromatography on silica

Sources & evidence

ORD record
ord-4fa3052cb8fd41bd9be7041c77dd0d22
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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