2-Methoxyaniline → HCID 10559737, compound

HRID 2392633Notes

Reaction equation

HRID 2392633 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.Cl.[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14]Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][NH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 10340Sodium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 10559737HCID 10559737, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Anisidine (5.9 ml, 0.05 mole) and 2-dimethylaminoethyl chloride hydrochloride (5.0 g, 0.035 mole) were dissolved in ethanol (75 ml) and treated with sodium carbonate (7.42 g, 0.07 mole). The mixture was heated under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered, and the filtrate evaporated in vacuo. The residue was dissolved in H2O and 10% NaOH solution was added until basic. The mixture was extracted into Et2O, dried (Na2SO4) and evaporated in vacuo to give an orange oil. This was purified by flash column chromatography, eluting with ethyl acetate to afford the title compound as a pale orange oil (3.28 g, 48%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 7 hours
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate evaporated in vacuo
  5. dissolutionThe residue was dissolved in H2O
  6. addition10% NaOH solution was added until basic
  7. extractionThe mixture was extracted into Et2O
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customto give an orange oil
  11. customThis was purified by flash column chromatography
  12. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-3091f7a5287442a3933d3f189c13f384
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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