Water → Methyl-2-(4-isopropylanilino)acetate

HRID 600919

Reaction equation

HRID 600919 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].C([O-])(=O)C.[Na+].O>CO>[CH3:16][O:15][C:13](=[O:14])[CH2:12][NH:8][C:7]1[CH:9]=[CH:10][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74644-IsopropylanilineHCID 60984Methyl bromoacetateHCID 517045Sodium Acetate

Product 1

HCID 22669181Methyl-2-(4-isopropylanilino)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-isopropylaniline (5.05 g, 37.3 mmol), methyl bromoacetate (5.99 g, 39.2 mmol) and anhydrous sodium acetate (3.21 g) in absolute methanol (30 mL) was heated to reflux for 2 h. The solution was cooled and poured into 300 mL water. The resulting solid was collected by filtration and recrystallized from ethanol/water to afford pure product, methyl-2-(4-isopropylanilino)acetate, m.p. 35-36° C. (4.53 g, 55%). 1H NMR (CDCl3, 300 MHz): δ 7.06 (2H, d, J=8.2 Hz), 6.57 (2H, d, J=8.2 Hz), 4.18 (1H, v br), 3.90 (2H, s), 3.78 (3H, s), 2.81 (1H, m, J=7.0 Hz), 1.20 (6H, d, J=7.0 Hz). Mass spectrum (ES+): m/z 209 (3), 208 (31), 148 (100).

Workup

  1. temperatureto reflux for 2 h
  2. temperatureThe solution was cooled
  3. filtrationThe resulting solid was collected by filtration
  4. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-e50f3c9221b4496aaeb61c34ae29e7ce
Source dataset
uspto-grants-2011_03
Patent number
US07902241B2

Linked notes

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