N-methyl-2-pyrrolidone → HCID 67215301, compound

HRID 2421037Notes

Reaction equation

HRID 2421037 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[C:3]=1[Cl:10].[CH3:11][N:12]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N>[Cl:10][C:3]1[C:4]([CH3:9])=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[C:11]#[N:12]

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 67215590HCID 67215590, compound

Product 1

HCID 67215301HCID 67215301, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

A stirred solution of 4-bromo-3-chloro-2-methylphenol (0.427 g), zinc cyanide (0.271 g), and tetrakis[triphenylphosphine]palladium (0.056 g) in N-methyl-2-pyrrolidinone (5 mL) was heated under microwave irradiation (150 W) at 130° C. for 35 min. The reaction mixture was filtered through anhydrous magnesium sulfate, partitioned between 1:2 ethyl acetate/diethyl ether (15 mL) and water (15 mL). The aqueous phase was re-extracted with 1:2 ethyl acetate/diethyl ether (2×15 mL). The organics were combined, washed with water (2×20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The compound was purified by column chromatography using 1:9 ethyl acetate/iso-hexane as eluent, to give the desired product as a peach coloured solid (174 mg, 54%).

Workup

  1. filtrationThe reaction mixture was filtered through anhydrous magnesium sulfate
  2. custompartitioned between 1:2 ethyl acetate/diethyl ether (15 mL) and water (15 mL)
  3. extractionThe aqueous phase was re-extracted with 1:2 ethyl acetate/diethyl ether (2×15 mL)
  4. washwashed with water (2×20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe compound was purified by column chromatography

Sources & evidence

ORD record
ord-6950b1edf6384f19bfe191c867636eda
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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