Water → 2-(Azetidin-1-yl)-5-nitropyridine

HRID 1019536Notes

Reaction equation

HRID 1019536 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.O>CN(C)C=O.C(OCC)(=O)C>[N:1]1([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 10422AzetidineHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 668504742-(Azetidin-1-yl)-5-nitropyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Add, dropwise, 4.7 g (80.76 mmol) of azetidine to a suspension, stirred at 20° C., of 27.9 g (0.201 mole) of potassium carbonate and 11 g (67.3 mmol) of 2-chloro-5-nitropyridine in 100 mL of dimethylformamide. Stir the mixture for 5 minutes at 20° C., then for 6 hours at 70° C. After this time, the suspension is poured into a mixture of 300 mL of water and 300 mL of ethyl acetate. The aqueous phase is separated, then extracted with 200 mL of ethyl acetate. The organic phases are combined, washed three times with 250 mL of water, then dried over sodium sulfate and concentrated at reduced pressure. We thus obtain 11.7 g of the expected product in the form of a solid.

Workup

  1. additionAdd
  2. waitfor 6 hours at 70° C
  3. customThe aqueous phase is separated
  4. extractionextracted with 200 mL of ethyl acetate
  5. washwashed three times with 250 mL of water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-7af908daae3043dda429c47b4453b2c1
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

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