Potassium Carbonate → 1-(6-Nitro-pyridin-3-yl)-azetidin-3-ol

HRID 1022199Notes

Reaction equation

HRID 1022199 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl.[NH:18]1[CH2:21][CH:20]([OH:22])[CH2:19]1>C(#N)C>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:18]2[CH2:21][CH:20]([OH:22])[CH2:19]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 167481095-Fluoro-2-nitropyridine

Product 1

HCID 592909581-(6-Nitro-pyridin-3-yl)-azetidin-3-olYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with acetonitrile (50 mL), 5-fluoro-2-nitropyridine (1.2 g, 7.9 mmol), K2CO3 (2.1 g, 15.8 mmol), and azetidin-3-ol hydrochloride (1.3 g, 11.9 mmol). The mixture was heated at 60° C. for 1 h. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (50:1 to 20:1) to afford 314a (1.1 g, 73%) as a yellow solid. MS-ESI: [M+H]+ 196.0.

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureAfter this time the reaction was cooled to room temperature
  3. filtrationIt was then filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with dichloromethane/methanol (50:1 to 20:1)

Sources & evidence

ORD record
ord-d05cfa45baa4436c90c260c1469f3158
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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