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

HRID 1512101Notes

Reaction equation

HRID 1512101 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 hydride2×HCID 783082-Chloro-5-nitropyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride and oil bath heating. 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 (MH+), 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-10f00b88449444f3a3776427f64defb7
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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