Ammonium formate → N1,5-Dimethylbenzene-1,2-diamine

HRID 875184Notes

Reaction equation

HRID 875184 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[N+:10]([O-])=O.C([O-])=O.[NH4+]>C1COCC1.CO.[Pd]>[CH3:9][C:7]1[CH:8]=[C:3]([NH:2][CH3:1])[C:4]([NH2:10])=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 10103510N,5-Dimethyl-2-nitroaniline

Product 1

HCID 9989323N1,5-Dimethylbenzene-1,2-diamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl-(5-methyl-2-nitro-phenyl)-amine (2.47 g, 14.9 mmol), ammonium formate (15 g, 237.9 mmol) in THF (7 mL) and MeOH (35 mL) at room temperature was added 10% Pd/C (650 mg) and the resulting mixture was stirred at room temperature for 10 min. The resulting mixture was then filtered over CELITE® and concentrated in vacuo. The resulting residue was diluted with CH2Cl2, washed with H2O and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resultant residue was purified by flash column chromatography (SiO2), eluting with a hexanes-EtOAc gradient to yield 4,N2-dimethyl-benzene-1,2-diamine

Workup

  1. filtrationThe resulting mixture was then filtered over CELITE®
  2. concentrationconcentrated in vacuo
  3. additionThe resulting residue was diluted with CH2Cl2
  4. washwashed with H2O
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by flash column chromatography (SiO2)
  9. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-2af94fba203d4beea7acf00da0dca1c6
Source dataset
uspto-grants-2015_03
Patent number
US08981113B2

Reaction notes

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