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

HRID 1512102
Notes
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Reaction equation

HRID 1512102 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-6d36d18db29343cdaac6c9c4545724fb
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08217035B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes