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

HRID 381206Notes

Reaction equation

HRID 381206 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C>C(#N)C.CCOCC>[CH3:8][N:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 3

HCID 7515N-MethylanilineHCID 7748Ethyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 265936(Methyl-phenyl-amino)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 16.7 g (100 mmol) of ethyl bromoacetate, 10.7 g (100 mmol) of N-methylaniline, and 12.9 g (100 mmol) of N,N-diisopropylethylamine in 100 mL of acetonitrile was allowed to stand for 24hr. and then diluted with 200 ml of ether. The amine salt was filtered and the filtrate concentrated, dissolved in 150 ml of CH2Cl2, washed with water, filtered through a plug of sodium sulfate/silica and distilled: 15.5 g (80%), b.p. 132°/12 mm.

Workup

  1. filtrationThe amine salt was filtered
  2. concentrationthe filtrate concentrated
  3. dissolutiondissolved in 150 ml of CH2Cl2
  4. washwashed with water
  5. filtrationfiltered through a plug of sodium sulfate/silica
  6. distillationdistilled

Sources & evidence

ORD record
ord-e2aa5949263c41908cefd6a9f8769616
Source dataset
uspto-grants-2001_10
Patent number
US06306570B1

Reaction notes

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