Potassium Carbonate → HCID 89924214, compound

HRID 1500919Notes

Reaction equation

HRID 1500919 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[NH2:12][CH:13]1[CH2:17][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:15](=[O:27])[CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:12][CH:13]2[CH2:17][N:16]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:15](=[O:27])[CH2:14]2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 20110077HCID 20110077, compound

Product 1

HCID 89924214HCID 89924214, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-chloro-1-fluoro-2-nitrobenzene (9.2 g, 52.4 mmol), 4-amino-1-(4-methoxybenzyl)pyrrolidin-2-one (11.5 g, 52.4 mmol) and K2CO3 (14.5 g, 105 mmol) in 300 mL of anhydrous CH3CN was heated with stirring at 50° C. for 16 hours. The reaction mixture was filtered and the filter cake was dissolved with H2O (400 mL), and extracted with EtOAc (200 mL×4). The organic layers and the filtrate was combined and concentrated in vacuo to 50 mL. The precipitate was collected by filtration and washed with 10 mL of PE to afford 4-[(4-chloro-2-nitrophenyl)amino]-1-(4-methoxybenzyl)pyrrolidin-2-one as an orange solid (15.8 g, yield: 80.2%).

Workup

  1. temperaturewas heated
  2. filtrationThe reaction mixture was filtered
  3. dissolutionthe filter cake was dissolved with H2O (400 mL)
  4. extractionextracted with EtOAc (200 mL×4)
  5. concentrationconcentrated in vacuo to 50 mL
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with 10 mL of PE

Sources & evidence

ORD record
ord-16a27f1b13604b4a84e05d1582a932ba
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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