2-(2-Dimethylaminoethoxy)-5-nitropyridine → 6-[2-(Dimethylamino)ethoxy]pyridin-3-amine

HRID 1043773Notes

Reaction equation

HRID 1043773 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[N:8][CH:9]=1)([O-])=O.[H][H]>CO.[Pd]>[CH3:14][N:13]([CH3:15])[CH2:12][CH2:11][O:10][C:7]1[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 529049082-(2-Dimethylaminoethoxy)-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 206914066-[2-(Dimethylamino)ethoxy]pyridin-3-amineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(5-Nitropyridin-2-yloxy)-N,N-dimethylethanamine (295 mg, 1.40 mmol) was dissolved in 5 mL of methanol and placed under a nitrogen atmosphere. A catalytic amount of 10% palladium on carbon was added and a hydrogen balloon was connected to the reaction flask. The flask was flushed five times with hydrogen and stirred at room temperature under hydrogen atmosphere for 16 hours. The solid was filtered and washed with methanol. The filtrate was evaporated under reduced pressure yielding 6-[2-(dimethylamino)ethoxy]pyridin-3-amine as a brown oil (250 mg, 99%). LC/MS (m/z): 182.1 (MH+), Rt 0.36 minutes.

Workup

  1. customThe flask was flushed five times with hydrogen
  2. filtrationThe solid was filtered
  3. washwashed with methanol
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a39d4ca8aa0044f593ddfd6df198905a
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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