Ammonium formate → 2-Methoxy-4-(2-pyrrolidin-1-ylethyl)phenylamine

HRID 871891Notes

Reaction equation

HRID 871891 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:16][CH2:17][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O>CO.[Pd]>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:16][CH2:17][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:10]=[CH:11][C:12]=1[NH2:13]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 673259461-[2-(3-Methoxy-4-nitrophenyl)ethyl]pyrrolidine

Product 1

HCID 673259262-Methoxy-4-(2-pyrrolidin-1-ylethyl)phenylamineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.41 g of palladium-on-charcoal and 4.1 g (64.32 mmol) of ammonium formate are added to a solution of 3.2 g (12.86 mmol) of the product prepared in step 24.2 in 120 mL of methanol, under argon, and the mixture is refluxed for 2 hours. After filtration, the filtrate is concentrated to dryness to give 2.6 g of the expected product in the form of a light-brown solid, which is used as obtained in the following step. Yield=92%.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. filtrationAfter filtration
  3. concentrationthe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-0d0a280b9d3244499faa01336aa8a3ee
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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