Potassium Carbonate → HCID 59452837, compound

HRID 419326Notes

Reaction equation

HRID 419326 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].Cl.Cl[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 162713-Nitro-p-cresolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 59452837HCID 59452837, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-Methyl-3-nitrophenol (2.0 g, 13 mmol), 1-chloro-2-dimethylaminoethane hydrochloride (3.8 g, 26 mmol), and K2CO3 (5.4 g, 39 mmol) were added to 2-butanone (30 mL). The mixture was refluxed for 12 h after which TLC analysis revealed consumption of the starting phenol. The reaction was cooled, diluted with saturated NH4Cl, and extracted with EtOAc. The organic layers were dried (Mg2SO4), filtered, concentrated, and purified via flash silica gel chromatography to afford the title compound (2.6 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.34 (s, 6H), 2.53 (s, 3H), 2.74 (t, J=5.6 Hz, 2H), 4.09 (t, J=5.5 Hz, 2H), 7.10 (dd, J=8.4, 2.7 Hz, 1H), 7.22 (d, J=8.6 Hz, 1H), 7.53 (d, J=2.6 Hz, 1H).

Workup

  1. temperatureThe mixture was refluxed for 12 h after which TLC analysis
  2. customconsumption of the starting phenol
  3. temperatureThe reaction was cooled
  4. additiondiluted with saturated NH4Cl
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layers were dried (Mg2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via flash silica gel chromatography

Sources & evidence

ORD record
ord-d110331b790f4407ab93a3e3564841df
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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