Hydrochloric Acid → 1-(4-Nitrophenyl)azetidine

HRID 594813Notes

Reaction equation

HRID 594813 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:14][CH2:13][CH2:12]1.Cl.C([O-])([O-])=O.[K+].[K+]>CCO>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9590p-FluoronitrobenzeneHCID 10422AzetidineHCID 11430Potassium Carbonate

Product 1

HCID 5917181-(4-Nitrophenyl)azetidineYield 11%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Fluoro-4-nitrobenzene (5.0 g, 35.5 mmol) was added to a suspension of azetidine.HCl (3.98 g, 42.55 mmol) and K2CO3 (7.34 g, 53.19 mmol) in EtOH (100 mL) at r.t., and the reaction was stirred at 40° C. overnight. The reaction mixture was filtered and concentrated. The residue was purified by silica gel chromatography (PE:EtOAc=10:1) to give compound 700 mg (11%) of the title compound as a yellow solid. [M+H] Calc'd for C9H10N2O2, 180. Found, 180.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-2e4e21d8f5d7468aae915371328ac9e4
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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