Stannous chloride dihydrate → N-(3-amino-5-bromophenyl)-N-methylacetamide

HRID 1603615Notes

Reaction equation

HRID 1603615 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:11]([CH3:15])[C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.O.O.Cl[Sn]Cl>C(O)C.Cl>[NH2:8][C:6]1[CH:5]=[C:4]([N:11]([CH3:15])[C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([Br:1])[CH:7]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 10683645N-(3-bromo-5-nitrophenyl)-N-methylacetamide

Product 1

HCID 10562181N-(3-amino-5-bromophenyl)-N-methylacetamideYield 59%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

4.5 g (0.0165 mol) of N-(3-bromo-5-nitrophenyl)-N-methylacetamide were dissolved in 75 ml of ethanol, treated while cooling with a solution of 15.0 g (0.0665 mol) of SnCl2.2H2O in 30 ml of HCl (37%) and stirred at room temperature for 18 hrs. Then, the solvent was removed, the residue was adjusted to pH 8 with sat. NaHCO3 solution, extracted with ethyl acetate and sat. sodium chloride solution and the organic phase was dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:2, 1:1 and finally 2:1. There were obtained 2.35 g (59%) of N-(3-amino-5-bromophenyl)-N-methylacetamide as light brown crystals. MS (EI): me/e=244,242 (C9H11BrN2O+).

Workup

  1. additiontreated
  2. customThen, the solvent was removed
  3. extractionextracted with ethyl acetate and sat. sodium chloride solution
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:2, 1:1 and finally 2:1

Sources & evidence

ORD record
ord-579fb267fd4a4ff388122121b7941819
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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