Dichloromethane → 1-(3-Amino-4,5-dimethoxyphenyl)ethanone

HRID 2254773Notes

Reaction equation

HRID 2254773 reaction equation
O.O.[Sn](Cl)Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:19](=[O:21])[CH3:20])[CH:11]=[C:12]([N+:16]([O-])=O)[C:13]=1[O:14][CH3:15].C(=O)([O-])O.[Na+].C(Cl)Cl>C(O)C>[NH2:16][C:12]1[C:13]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:9]=[C:10]([C:19](=[O:21])[CH3:20])[CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 41514731-(3,4-Dimethoxy-5-nitrophenyl)ethanone

Product 1

HCID 214591851-(3-Amino-4,5-dimethoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.3 g of tin dichloride dihydrate are added to 2.25 g of 3',4'-dimethoxy-5'-nitroacetophenone dissolved in 50 ml of ethanol, whereupon the mixture is stirred at 74° for 30 minutes. Thereupon, the reaction mixture is poured on to 100 g of ice, neutralized with about 300 ml of saturated sodium hydrogen carbonate solution and treated with 150 ml of methylene chloride. The mixture is filtered and the methylene chloride phase is separated. This is dried over sodium sulfate and evaporated, and the residue is recrystallized from ether/petroleum ether. There is obtained 5'-amino-3',4'-dimethoxyacetophenone of m.p. 63°-65°.

Workup

  1. filtrationThe mixture is filtered
  2. customthe methylene chloride phase is separated
  3. dry with materialThis is dried over sodium sulfate
  4. customevaporated
  5. customthe residue is recrystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-dc19ef560fcb43c7ae82077f2185eb8e
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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