Chlorosuccinimide → HCID 57437531, compound

HRID 2205913Notes

Reaction equation

HRID 2205913 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][CH:3]=1.[Cl:14]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][C:3]=1[Cl:14]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 676146Pyrrolidinone, (4-aminophenyl)-

Product 1

HCID 57437531HCID 57437531, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Aminophenyl)pyrrolidin-2-one (0.3 g, 1.7 mmol) and N-chlorosuccinimide (0.227 g, 1.7 mmol) were dissolved in acetonitrile (10 ml). The reaction was stirred and heated at reflux for 2 hours. The solvent was removed in vacuum and the residue purified by silica gel column chromatography eluting with 50% ethyl acetate in dichloromethane to afford the title compound as a white powder (0.16 g, 44.6%). 1H-NMR (500 MHz, CDCl3): δ 2.14 (m, 2H), 2.57 (t, J=8.3 Hz, 2H), 3.77 (t, J=7.1 Hz, 2H), 6.75 (d, J=8.7 Hz, 1H), 7.31 (dd, J=2.5 Hz, 8.7 Hz, 1H), 7.48 (d, J=2.5 Hz, 1H), 8.8 (s, 2H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuum
  4. customthe residue purified by silica gel column chromatography
  5. washeluting with 50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-f0307cf3d21549ed8c8101e0d16a0087
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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