1-Methyl-3-pyrrolidinol → HCID 67159330, compound

HRID 2234366Notes

Reaction equation

HRID 2234366 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13][N:14]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]1>C1(C)C=CC=CC=1.[OH-].[K+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[O:19][CH:16]1[CH2:17][CH2:18][N:14]([CH3:13])[CH2:15]1

Participants

6

Reactant 2

HCID 930741-Methyl-3-pyrrolidinolHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 67159330HCID 67159330, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-Fluoro-2-methoxy-1-nitrobenzene (Apollo Scientific; 4.28 g, 25 mmol) in toluene (20 mL) and 25% KOH aq. (20 mL), were added at room temperature, 1-methyl-3-pyrrolidinol (5.0 g, 50 mmol) and tetra-n-butylammonium bromide (1.66 g, 5 mmol). The mixture was heated at 60° C. for 18 hrs. The reaction mixture was cooled to room temperature, poured onto ice-water (200 mL) and extracted with Ethyl Acetate (3×100 mL). The organic layer was washed with 2 M HCl (250 ml) and then loaded onto a 50 g SCX-2 cartridge, washing with water and eluting with 7 N methanolic ammonia to give the title compound as a yellow oil, which solidified on standing (5.50 g, 87%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured onto ice-water (200 mL)
  3. extractionextracted with Ethyl Acetate (3×100 mL)
  4. washThe organic layer was washed with 2 M HCl (250 ml)
  5. washwashing with water
  6. washeluting with 7 N methanolic ammonia

Sources & evidence

ORD record
ord-19ba1f8e0eef4a46ba6e53da3076d6e7
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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