Ammonium formate → 2-(3-methoxypropoxy)benzenamine

HRID 1176209Notes

Reaction equation

HRID 1176209 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 685007031-(3-Methoxypropoxy)-2-nitrobenzene

Product 1

HCID 261890962-(3-methoxypropoxy)benzenamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2.55 g of 1-(3-methoxypropoxy)-2-nitrobenzene, 3.72 g of ammonium formate in 25 ml of methanol is hydrogenated at reflux in the presence of 0.26 g of 10% Pd/C over 1.5 hours. The reaction mixture is cooled and clarified by filtration, and the filtrate is concentrated by evaporation. The residue is dissolved in diethyl ether, washed with water (2×) and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a red oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.30 (1:2 EtOAc-heptane); Rt=2.28.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationclarified by filtration
  3. concentrationthe filtrate is concentrated by evaporation
  4. dissolutionThe residue is dissolved in diethyl ether
  5. washwashed with water (2×) and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1b87fe8f97a641bcb766f6c75bb2c49e
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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