Potassium Carbonate → HCID 58827300, compound

HRID 448388Notes

Reaction equation

HRID 448388 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][CH2:16][CH2:15][N:14]([CH3:18])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride2×

Product 1

HCID 58827300HCID 58827300, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3-fluoro-4-nitrophenol (3.0 g, 19 mmol), 2-(dimethylamino)ethyl chloride hydrochloride (3.0 g, 21 mmol) and potassium carbonate (5.4 g, 39 mmol) in 2-butanone (75 mL) was heated to reflux for 20 hours. An additional portion of 2-(dimethylamino)ethyl chloride hydrochloride (2.0 g, 14 mmol) was added, and stirring at reflux proceeded for 24 hours. The mixture was cooled and evaporated under vacuum, and the residue was partitioned between ethyl acetate (100 mL) and water (150 mL), and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (3×150 mL) and extracted into dilute aqueous HCl (3×75 mL). The combined aqueous extracts were washed with ethyl acetate (2×100 mL) and basified (NaOH), and the resulting mixture was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (3×100 mL), dried (MgSO4), and evaporated, providing 2.9 g as a yellow oil, in 67% yield; 1H NMR (CDCl3) δ 2.34 (s, 6H), 2.76 (t, J=5.5 Hz, 2H), 4.13 (t, J=5.5 Hz, 2H), 6.72-6.81 (m, 2H), 8.09 (t, J=9.1 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureat reflux
  4. temperatureThe mixture was cooled
  5. customevaporated under vacuum
  6. customthe residue was partitioned between ethyl acetate (100 mL) and water (150 mL)
  7. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
  8. washThe combined organic layers were washed with water (3×150 mL)
  9. extractionextracted into dilute aqueous HCl (3×75 mL)
  10. washThe combined aqueous extracts were washed with ethyl acetate (2×100 mL)
  11. extractionthe resulting mixture was extracted with ethyl acetate (3×100 mL)
  12. washThe combined extracts were washed with water (3×100 mL)
  13. dry with materialdried (MgSO4)
  14. customevaporated
  15. customproviding 2.9 g as a yellow oil

Sources & evidence

ORD record
ord-f692fa10ea16493fb2f5101f6ada55b2
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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