Gamma-Butyrolactone → 1-(2H-1,3-Benzodioxol-5-yl)pyrrolidin-2-one

HRID 1388335Notes

Reaction equation

HRID 1388335 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[C:11]1(=O)[O:15][CH2:14][CH2:13][CH2:12]1>>[O:10]1[C:9]2[CH:8]=[CH:7][C:5]([N:6]3[CH2:11][CH2:12][CH2:13][C:14]3=[O:15])=[CH:4][C:3]=2[O:2][CH2:1]1

Participants

3

Reactant 2

HCID 7302Gamma-ButyrolactoneHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 130503821-(2H-1,3-Benzodioxol-5-yl)pyrrolidin-2-oneYield 51%

Procedure

A mixture of 3,4-(methylenedioxy)aniline (200 g, 1.46 mole) and γ-butyrolactone (225 ml) was heated (in a dry nitrogen atmosphere) with stirring in a 200° oil bath for 2 days. Product was isolated from the reaction mixture by distillation under reduced pressure (b.p. 156°, 33 μ). Product was filtered over Silica Gel 60 (Trade Name) eluting with ethylacetate. The eluant was concentrated and the crystalline product was collected and washed with ether and petroleum ether affording 1-(1,3-benzodioxol-5-yl)-2-pyrrolidinone (153.4 g; 51%), m.p. 89°-91° which was one spot on tlc analysis.

Workup

  1. temperaturewas heated (in a dry nitrogen atmosphere)
  2. customProduct was isolated from the reaction mixture by distillation under reduced pressure (b.p. 156°, 33 μ)
  3. filtrationProduct was filtered over Silica Gel 60 (Trade Name)
  4. washeluting with ethylacetate
  5. concentrationThe eluant was concentrated
  6. customthe crystalline product was collected
  7. washwashed with ether and petroleum ether

Sources & evidence

ORD record
ord-8fd80c0602794eaf866397578b6cbd1e
Source dataset
uspto-grants-1984_02
Patent number
US04431662

Reaction notes

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