Acetic Acid → HCID 66898407, compound

HRID 75492Notes

Reaction equation

HRID 75492 reaction equation
[C:1]([NH:4][CH:5]([C:11](=O)[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2].[NH2:14][C:15]1C=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.C(#[N:29])CCC>>[CH3:2][C:1]1[N:29]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)[C:11]([CH3:12])=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:4]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6115Aniline2×HCID 8008ButyronitrileHCID 224840Ethyl 2-acetamido-3-oxobutanoate2×

Product 1

HCID 66898407HCID 66898407, compoundYield 14%

Procedure

To a solution of ethyl 2-acetamido-3-oxobutanoate (compound 10, 2.0 g, 10.6 mmol), aniline (compound 11b, 2.0 g, 21.3 mmol) in butyronitrile (15 mL) was added acetic acid (1.2 mL, 21.3 mmol) at room temperature. The reaction mixture was irradiated in a microwave reactor (Biotage Initiator™) for 40 minutes at 160° C. The mixture was concentrated under reduced pressure. The crude product was purified by preparative HPLC (purification system, Gilson) to provide the title compound (340 mg, 14%) as a brown oil.

Workup

  1. customThe reaction mixture was irradiated in a microwave reactor (Biotage Initiator™) for 40 minutes at 160° C
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe crude product was purified by preparative HPLC (purification system, Gilson)

Sources & evidence

ORD record
ord-52a68b798fae441ea2d906e988d54bbc
Source dataset
uspto-grants-2014_09
Patent number
US08835436B2

Reaction notes

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