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

HRID 1948777Notes

Reaction equation

HRID 1948777 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-nitropyridineYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

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

Workup

  1. waitfor 6 hours at 70° C
  2. waitAfter this period of time
  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 sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-027886f2251c40ce95831da50bc7b6e9
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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