N,N-Dimethylaniline → HCID 60589021, compound

HRID 1754998Notes

Reaction equation

HRID 1754998 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH:5](Br)[CH3:6])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[CH3:17].CN(C)C1C=CC=CC=1>>[CH2:1]([O:3][C:4](=[O:8])[CH:5]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[C:11]([CH3:17])[CH:12]=1)[CH3:6])[CH3:2]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 233594-Bromo-3-methylanilineHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 60589021HCID 60589021, compound

Conditions

Temperature
60 °C

Procedure

2-Bromo-propionic acid ethyl ester (973 mg, 5.22 mmol) was added to 4-bromo-3-methyl-phenylamine (1.00 g, 5.37 mmol) and dimethylphenylamine (682 μL, 5.37 mmol) at room temperature, and the mixture was stirred at 60° C. for 15 hours. The reaction solution was then cooled and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-(4-bromo-3-methyl-phenylamino)-propionic acid ethyl ester as a yellow form (1.38 g, 90%).

Workup

  1. temperatureThe reaction solution was then cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a9e3e4827dbf4718ba4fb888dbde1021
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…