Potassium Carbonate → 1-(5-Nitropyridin-2-yl)azetidin-3-ol

HRID 2236194Notes

Reaction equation

HRID 2236194 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.[OH:12][CH:13]1[CH2:16][NH:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:16][CH:13]([OH:12])[CH2:14]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 529372641-(5-Nitropyridin-2-yl)azetidin-3-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-5-nitropyridine (406 mg, 2 mmol), 3-hydroxyazetidine hydrochloride (199 mg, 2 mmol), and finely ground potassium carbonate (828 mg, 6 mmol) were heated to 80° C. in 20 mL anhydrous DMF for 5 hrs. The mixture was diluted with EtOAc, extracted with H2O and dried over MgSO4. The EtOAc layer was filtered, evaporated to dryness and used without further purification. ES-MS calcd for C8H9N3O3 (m/e) 195.18, obsd 196.2 (M+H).

Workup

  1. extractionextracted with H2O
  2. dry with materialdried over MgSO4
  3. filtrationThe EtOAc layer was filtered
  4. customevaporated to dryness
  5. customused without further purification

Sources & evidence

ORD record
ord-9d6b97894734447a9b556f181e249089
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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