Dimethyl-[2-(3-nitro-pyrrol-1-yl)-ethyl]amine → HCID 66914619, compound

HRID 43157Notes

Reaction equation

HRID 43157 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6]1>[Ni].CO.C1COCC1>[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6]1

Participants

4

Reactant 1

HCID 66914587Dimethyl-[2-(3-nitro-pyrrol-1-yl)-ethyl]amine

Product 1

HCID 66914619HCID 66914619, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A suspension of dimethyl-[2-(3-nitro-pyrrol-1-yl)-ethyl]-amine (Step 121.2) (650 mg, 3.55 mmol) and Raney Nickel (300 mg) in MeOH/THF (1:1, v/v; 150 mL) was stirred for 7 h at rt, under a hydrogen atmosphere. The mixture was filtered through a pad of celite and the filtrate was concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 98:1:1→93:6:1) to afford 440 mg of the title compound as a red oil. Title compound: ESI-MS: 154.1 [M+H]+; TLC: Rf=0.02 (DCM/MeOH, 9:1).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 98:1:1→93:6:1)

Sources & evidence

ORD record
ord-c355854a24f043f28ebcc5871d45c5b2
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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