Stannous chloride dihydrate → 1-(3,4-diaminophenyl)ethanone

HRID 555422Notes

Reaction equation

HRID 555422 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1)=[O:3].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[NH2:11][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH3:1])[CH:9]=[CH:8][C:7]=1[NH2:10]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 115863891-(4-amino-3-nitrophenyl)ethanone

Product 1

HCID 4327231-(3,4-diaminophenyl)ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methylcarbonyl-2-nitro-benzenamine (500 mg, 2.775 mmol) in EtOAc (16 mL) was added SnCl2.2H2O (3.130 g, 13.88 mmol). The reaction mixture was refluxed for 2.5 h, cooled to rt, and diluted with H2O (130 mL). The pH of the mixture was adjusted to 7-8 by addition of saturated NaHCO3 solution and the aqueous phase was extracted with EtOAc (2×120 mL). The combined organic extracts were washed with brine (2×60 mL) and dried over MgSO4. After the removal of the solvent under vacuum, 142a was obtained as a red orange solid (418 mg).

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 h
  2. extractionthe aqueous phase was extracted with EtOAc (2×120 mL)
  3. washThe combined organic extracts were washed with brine (2×60 mL)
  4. dry with materialdried over MgSO4
  5. customAfter the removal of the solvent under vacuum

Sources & evidence

ORD record
ord-ca0b7a9dd9b24df397a66ed41808e721
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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