N-methyl-2-pyrrolidone → HCID 90028954, compound

HRID 2200118Notes

Reaction equation

HRID 2200118 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CC([O-])(C)C.[K+].CN1CCCC1=O.[Cl:25][C:26]1[CH:31]=[C:30](F)[CH:29]=[CH:28][N:27]=1>CCOC(C)=O>[Cl:25][C:26]1[CH:31]=[C:30]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH:29]=[CH:28][N:27]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 162713-Nitro-p-cresolHCID 27827922-Chloro-4-fluoropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 90028954HCID 90028954, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add 4-methyl-3-nitrophenol (6.95 g, 45.46 mmol) and t-BuOK (5.94 g, 53.03 mmol) to N-methylpyrrolidin-2-one (100 mL), stir for 30 min, then add 2-chloro-4-fluoro-pyridine (5 g, 37.88 mmol) and stir the reaction at 70° C. overnight. TLC (PE:EtOAc=3:1) shows the reaction is complete. Add water (250 mL) to the reaction mixture, extract with EtOAc (100 mL×4), combine the organic layers, wash with water, brine respectively and dry over Na2SO4. Concentrate to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:4) affords the title compound (5.8 g, 58%). MS: (M+1): 265.1.

Workup

  1. customthe reaction at 70° C. overnight
  2. extractionAdd water (250 mL) to the reaction mixture, extract with EtOAc (100 mL×4)
  3. washwash with water, brine respectively
  4. dry with materialdry over Na2SO4
  5. concentrationConcentrate
  6. customto give the crude product
  7. customPurification by chromatography (silica gel, EtOAc:PE=1:4)

Sources & evidence

ORD record
ord-ce6cce99b0cf43ac9232e17aca42c4e3
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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