3,5-Dimethylaniline → HCID 24801206, compound

HRID 269745Notes

Reaction equation

HRID 269745 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].Br[CH2:11][CH2:12][OH:13].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:11][CH2:12][OH:13])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 79493,5-DimethylanilineHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 24801206HCID 24801206, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,5-dimethyl-aniline (0.04 mol), 2-bromo-ethanol (0.033 mol) and K2CO3 (0.033 mol) in CH3CN (50 ml) was stirred at 80° C. for 12 hours. The reaction was cooled down to room temperature and the solvent was evaporated. The residue was taken up in CH2Cl2/CH3OH (95/5) and washed with a saturated solution of K2CO3 in water. The organic layer was separated, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98/2/0.1; 20-45 μm). The pure fractions were collected and the solvent was evaporated, yielding 1.9 g of 2-(3,5-dimethyl-phenylamino)-ethanol (29%).

Workup

  1. temperatureThe reaction was cooled down to room temperature
  2. customthe solvent was evaporated
  3. washwashed with a saturated solution of K2CO3 in water
  4. customThe organic layer was separated
  5. dry with materialdried (over MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated until dryness
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98/2/0.1; 20-45 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c3e2f937f5e0427f847cbf59bbc42f2b
Source dataset
uspto-grants-2008_11
Patent number
US07449463B2

Reaction notes

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