Ammonium formate → 1-(2-Amino-4-methylphenyl)ethan-1-one

HRID 1432862Notes

Reaction equation

HRID 1432862 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:11][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[C:8](=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 217823221-(4-Methyl-2-nitrophenyl)ethanone

Product 1

HCID 139308231-(2-Amino-4-methylphenyl)ethan-1-oneYield 107.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-methyl-2-nitrophenylethanone (5.0 g, 28 mmol) in methanol (100 mL) is treated with ammonium formate (9.6 g, 140 mmol) and 5% palladium on carbon (1.5 g). The mixture is heated to 60° C. for 6 h then stirred at ambient temperature for 16 hours. The reaction mixture is filtered through Celite and the filtrate is concentrated in vacuo. The concentrate is treated with sodium bicarbonate and partitioned between water and ethyl acetate. The organic layer is separated, dried with sodium sulfate and concentrated to give crude title compound (4.5 g, 30.2 mmol) which is used without further purification. MS m/z: M+=149; 1H NMR (CDCl3, 300 MHz) δ8.05 (d, 1H), 7.4 (d, 1H), 7.25 (s, 1H), 2.8 (s, 3H), 2.45 (s, 3H).

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. additionThe concentrate is treated with sodium bicarbonate
  4. custompartitioned between water and ethyl acetate
  5. customThe organic layer is separated
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2fc445ff2e3d442b962a1636807b4cc1
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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