N-Methylaniline → (Methyl-phenyl-amino)-acetic acid ethyl ester

HRID 352197

Reaction equation

HRID 352197 reaction equation
Br[CH2:2][CH2:3][O:4][C:5](=[O:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH2:3]([O:4][C:5](=[O:7])[CH2:6][N:15]([CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethane

Product 1

HCID 265936(Methyl-phenyl-amino)-acetic acid ethyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bromoethylacetate, 3.3 mL (30.0 mmol) in 100 mL of tetrahydrofuran was added 4.14 g (30.0 mmol) of potassium carbonate and 3.25 mL of N-methylaniline. The reaction mixture stirred overnight at rt. and was concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by column chromatography using EtOAc/hexanes as eluent and concentrated to dryness to give 4.74 g (82%) of the desired product as a tan oil. MS (ion spray) 194.1 (M+1).

Workup

  1. concentrationand was concentrated to dryness
  2. customThe residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3
  3. washThe mixture was washed with saturated NaHCO3
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2e69b577dcc348c98e5d4282115c8492
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

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