2-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole → 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-ylamine

HRID 1189746Notes

Reaction equation

HRID 1189746 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=[CH:7][N:8]=1)([O-])=O>[Pd].CO>[CH3:14][Si:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][O:10][CH2:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[NH2:1]

Participants

4

Reactant 1

HCID 143583852-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

Product 1

HCID 669145481-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-ylamineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (Step 14.3) (1.84 g, 7.57 mmol) and palladium on carbon (200 mg) in MeOH (30 mL) was stirred for 40 min at rt, under a hydrogen atmosphere. The reaction mixture was filtered through a pad of celite and concentrated to afford 1.55 g of the title compound: ESI-MS: 214.1 [M+H]+; tR=3.26 min (System 1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-090e6760978a473480fa333799c39fdb
Source dataset
uspto-grants-2014_03
Patent number
US08674099B2

Reaction notes

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