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

HRID 1512100Notes

Reaction equation

HRID 1512100 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1>CN(C=O)C.O.CCOC(C)=O>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:19][CH:20]=1)([O-:26])=[O:25]

Participants

7

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 783082-Chloro-5-nitropyridineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 529049082-(2-Dimethylaminoethoxy)-5-nitropyridineYield 44.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Microwave heating. To a solution of 2-(dimethylamino)ethanol (339 mg, 3.80 mmol) in DMF (5 mL) was added sodium bis(trimethylsilyl)amide (4.75 mL, 1M solution in THF, 4.75 mmol). The mixture was stirred at room temperature for 15 min. 2-Chloro-5-nitropyridine (500 mg, 3.16 mmol) was then added. The vial was capped and subjected to microwave irradiation (150° C. for 10 minutes). The mixture was diluted with water (250 mL) and EtOAc (250 mL). The two layers were separated, and the aqueous layer extracted two more times with EtOAc. The organic extracts were combined, washed with water and brine, dried over sodium sulfate and evaporated to give the crude material as brown oil. Purification by column chromatography on silica gel using 5% methanol/methylene chloride yielded 2-(5-nitropyridin-2-yloxy)-N,N-dimethylethanamine as a light yellow solid (295 mg, 44%).

Workup

  1. temperatureMicrowave heating
  2. customThe vial was capped
  3. customsubjected to microwave irradiation (150° C. for 10 minutes)
  4. customThe two layers were separated
  5. extractionthe aqueous layer extracted two more times with EtOAc
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give the crude material as brown oil
  10. customPurification by column chromatography on silica gel using 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-54e7667f7ee14757bf3af95592da0362
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

Loading…