Stannous chloride dihydrate → 5-Chloro-N1-Methylbenzene-1,2-diaMine

HRID 1710658Notes

Reaction equation

HRID 1710658 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([NH:8][CH3:9])[CH:7]=1.O.O.Cl[Sn]Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 2580415-chloro-N-methyl-2-nitroaniline

Product 1

HCID 121982665-Chloro-N1-Methylbenzene-1,2-diaMine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of (5-chloro-2-nitro-phenyl)-methyl-amine (59) (500 mg, 2.7 mmol, 1 eq), SnCl2.2H2O (3.0 g, 13.3 mmol, 5 eq) in ethyl acetate (25 ml) was refluxed overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated potassium carbonate solution. The organic phase was concentrated and the crude residue was purified with flash chromatography to give 4-chloro-N2-methyl-benzene-1,2-diamine (60).

Workup

  1. temperaturewas refluxed overnight
  2. washwashed with saturated potassium carbonate solution
  3. concentrationThe organic phase was concentrated
  4. customthe crude residue was purified with flash chromatography

Sources & evidence

ORD record
ord-e601213018954e3aae6e7e274ee22c62
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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