2,5-Dimethylaniline → N-(2,5-dimethylphenyl)-3-oxobutanamide

HRID 2368701Notes

Reaction equation

HRID 2368701 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[O:10]=[C:11]([CH3:18])[CH2:12][C:13](OCC)=[O:14]>>[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH:4][C:13](=[O:14])[CH2:12][C:11](=[O:10])[CH3:18]

Participants

3

Reactant 2

HCID 72592,5-DimethylanilineHCID 8868Ethyl Acetoacetate

Product 1

HCID 284876N-(2,5-dimethylphenyl)-3-oxobutanamide

Procedure

A mixture of 2,5-dimethylaniline (1.00 g, 8.25 mmol) and ethyl 3-oxobutanoate (1.0 mL, 1.0 eq) was microwaved at 180° C. for 5 minutes. 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 title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 2.28 (s, 3 H) 2.32 (s, 3 H) 2.34 (s, 3 H) 3.63 (s, 2 H) 6.88 (d, J=7.62 Hz, 1 H) 7.07 (d, J=7.62 Hz, 1 H) 7.75 (s, 1 H) 9.00-9.12 (m, 1 H).

Workup

  1. customwas microwaved at 180° C. for 5 minutes
  2. customit was triturated with hexane
  3. filtrationThe resulting precipitate was filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-17044b7e4d8548f7bc063be8703bf980
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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