2,5-Dimethylaniline → N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide

HRID 1892262

Reaction equation

HRID 1892262 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[CH3:10][CH:11]([CH3:20])[C:12](=[O:19])[CH2:13][C:14](OCC)=[O:15]>>[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH:4][C:14](=[O:15])[CH2:13][C:12](=[O:19])[CH:11]([CH3:20])[CH3:10]

Participants

3

Reactant 2

HCID 72592,5-DimethylanilineHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 86669288N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide

Conditions

Temperature
160 °C

Procedure

A mixture of 2,5-dimethylaniline (7.70 g, 63.54 mmol) and ethyl 4-methyl-3-oxopentanoate (10.00 g, 1.0 eq) were refluxed at 160° C. overnight. After the reaction mixture was cooled to room temperature, it was triturated with hexane. The resulting precipitate was filtered and dried under high vacuum to yield the desired N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.18 (d, J=7.03 Hz, 6 H) 2.30 (d, J=7.62 Hz, 6 H) 2.66-2.85 (m, 1 H) 3.64 (s, 2 H) 6.87 (d, J=8.50 Hz, 1 H) 7.06 (d, J=7.62 Hz, 1 H) 7.77 (s, 1 H) 9.13 (br. s., 1 H).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customit was triturated with hexane
  3. filtrationThe resulting precipitate was filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-b3ae5ecf57f947018f8a7e9a6734c8df
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Linked notes

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