N-Methylaniline → HCID 20477404, compound

HRID 905121Notes

Reaction equation

HRID 905121 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C1C=CC=CC=1>[CH3:1][N:2]([CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 69637Diethyl bromomalonate

Product 1

HCID 20477404HCID 20477404, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-methylaniline (15.1 g), diethyl bromomalonate (16.9 g) and dry benzene (90 ml) were mixed and heated under reflux for 16 hours with stirring. The reaction mixture was washed, dried and concentrated by the same procedure as in Example 2, (1). The residue was purified by silica gel column chromatography using benzene/hexane (2:1) as an eluent to give 10.2 g (yield 54%) of diethyl N-methylanilinomalonate having the following NMR data.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. washThe reaction mixture was washed
  4. customdried
  5. concentrationconcentrated by the same procedure as in Example 2, (1)
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1911ddc0800740959963d478f3d86599
Source dataset
uspto-grants-1983_12
Patent number
US04421914

Reaction notes

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