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

HRID 274501Notes

Reaction equation

HRID 274501 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 75° 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-a4f1f7d70e804d90a37f03f52822f975
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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