Stannous Chloride → HCID 88201970, compound

HRID 2269426Notes

Reaction equation

HRID 2269426 reaction equation
[CH2:1]([O:8][N:9]=[C:10]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=1)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)Cl>C(O)C>[CH2:1]([O:8][N:9]=[C:10]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 88201839HCID 88201839, compound

Product 1

HCID 88201970HCID 88201970, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of isomer A of 4-methoxyphenyl 3-nitrophenyl ketone O-benzyloxime (974 mg) [prepared as described in step (a) above] and tin (II) chloride (2.55 g) in ethanol (30 ml) was heated under reflux for 1 hour. After removal of the ethanol by evaporation, the residue was diluted with ethyl acetate. The ethyl acetate was washed with a 5N aqueous solution of sodium hydroxide, with water and then with a saturated aqueous solution of sodium chloride. It was then dried over anhydrous magnesium sulfate and evaporated under reduced pressure, to afford isomer A of the title compound (893 mg) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customAfter removal of the ethanol
  4. customby evaporation
  5. additionthe residue was diluted with ethyl acetate
  6. washThe ethyl acetate was washed with a 5N aqueous solution of sodium hydroxide, with water
  7. dry with materialIt was then dried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8ecd02f7a4d84de8acf034e81907a62e
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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