2-(Dimethylamino)ethanol → 2-(2-Dimethylaminoethoxy)-5-nitropyridine

HRID 1043772Notes

Reaction equation

HRID 1043772 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=1.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][OH:17]>O1CCCC1>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([O:17][CH2:16][CH2:15][N:14]([CH3:18])[CH3:13])=[N:5][CH:6]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 529049082-(2-Dimethylaminoethoxy)-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of sodium hydride (189 mg, 4.73 mmol) in anhydrous tetrahydrofuran (2 mL) at 0° C. a solution of 2-chloro-5-nitropyridine (500 mg, 3.16 mmol) and 2-(dimethylamino)ethanol (353 mg, 3.96 mmol) in anhydrous tetrahydrofuran (4 mL) was added dropwise. The reaction was warmed to room temperature and stirred for 16 h. The THF was evaporated, and water (100 mL) and EtOAc (200 mL) were added. The aqueous layer was extracted with EtOAc (200 mL), and the organic layers combined, washed with brine, dried over sodium sulfate and concentrated to give a brown oil. Purification column chromatography on silica gel using 5% methanol/methylene chloride yielded 2-(5-nitropyridin-2-yloxy)-N,N-dimethylethanamine as a light yellow solid (233=mg, 35%). LC/MS (m/z): 212.2 (Ma), Rt 1.28 minutes.

Workup

  1. additionwas added dropwise
  2. customThe THF was evaporated
  3. additionwater (100 mL) and EtOAc (200 mL) were added
  4. extractionThe aqueous layer was extracted with EtOAc (200 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customPurification column chromatography on silica gel using 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-55678a138e3d4f67ae392cf48c29dc6d
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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