HCID 86659877, compound → HCID 86659878, compound

HRID 2360157Notes

Reaction equation

HRID 2360157 reaction equation
[CH2:1]([N:8]([CH2:17][C:18](=O)[CH3:19])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Cl-].[Zn+2].[Cl-]>[CH2:1]([N:8]1[C:9]2[C:14](=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:18]([CH3:19])=[CH:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86659877HCID 86659877, compound

Product 1

HCID 86659878HCID 86659878, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of 1-[N-benzyl-N-(4-methoxyphenyl)amino]propan-2-on (863 mg, 3.20 mmol) in 9.6 mL of ethanol was added zinc chloride (1.3 g, 9.6 mmol) at room temperature. After the reaction mixture was stirred over night, zinc chloride (1.3 g, 9.6 mmol) was added with additional stirring for 10 h. After the reaction mixture was concentrated in vacuo, the residue was diluted with ethyl acetate, and washed with water, 1 M HCl, saturated NaHCO3 aqueous solution and brine, successively, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain the title compound (503 mg, 62%).

Workup

  1. stirringwith additional stirring for 10 h
  2. concentrationAfter the reaction mixture was concentrated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with water, 1 M HCl, saturated NaHCO3 aqueous solution and brine
  5. dry with materialsuccessively, and dried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-206baa52ec1a4a48a8a01eda742be98b
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

Loading…