Ammonia → 2-Pyrrolidinone, 1-(8-quinolinyl)-

HRID 1902829Notes

Reaction equation

HRID 1902829 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13].[As+3]=O.[CH:16]([CH:18]=[CH2:19])=O.N>S(=O)(=O)(O)O.O>[N:1]1[C:2]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:19]=[CH:18][CH:16]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7847Acrolein2×HCID 70640001-(2-aminophenyl)pyrrolidin-2-oneHCID 178514815HCID 178514815, compound

Product 1

HCID 30614652-Pyrrolidinone, 1-(8-quinolinyl)-Yield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 1-(2-aminophenyl)-2-pyrrolidinone (J. Chem. Soc. C, 1969 (10), 1444-8) (3.2 g, 0.018 mole) and arsenic (V) oxide (2.5 g, 0.011 mole) in aqueous sulphuric acid (concentrated sulphuric acid (4.0 ml) in water (1.3 ml)) was heated to 70° and stirred vigorously. Acrolein (2.5 ml, 0.037 mole) was added dropwise at a rate such that the reaction temperature did not exceed 95°. The reaction temperature was maintained at 95° to 115° by heating and stirring in a nitrogen atmosphere for 1 hour after addition of acrolein was complete. The product was poured into water and the pH was adjusted to pH 6 with concentrated ammonia. Extraction of the aqueous solution with methylene chloride, after removal of the solvent, afforded an oil. Separation was achieved by column chromatography (200 g SILICA GEL 60 (Trade Name)). The oil was eluted first with acetone/ethyl acetate (30:70) then acetone/ethyl acetate (50:50) and finally acetone. The solvet was removed from the acetone/ethyl acetate (50:50) and the acetone fractions to afford a homogeneous solid as shown by tlc analysis. Crystallization from acetone afforded 1-(8-quinolyl)-2-pyrrolidinone (m.p. 121° -122°), yield 21%. Analysis of the sample by tlc and NMR as well as elemental analysis verified the identity of this material with that obtained in Example 1.

Workup

  1. temperaturewas heated to 70°
  2. customdid not exceed 95°
  3. temperatureThe reaction temperature was maintained at 95° to 115°
  4. temperatureby heating
  5. stirringstirring in a nitrogen atmosphere for 1 hour
  6. extractionExtraction of the aqueous solution with methylene chloride
  7. customafter removal of the solvent
  8. customafforded an oil
  9. customSeparation
  10. washThe oil was eluted first with acetone/ethyl acetate (30:70)
  11. customThe solvet was removed from the acetone/ethyl acetate (50:50)
  12. customthe acetone fractions to afford a homogeneous solid
  13. customCrystallization from acetone

Sources & evidence

ORD record
ord-5ceea441b14e4e5996745e8b04143296
Source dataset
uspto-grants-1982_12
Patent number
US04366158

Reaction notes

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