Water → N-(4-Cyano-2-nitrophenyl)-4-pentenamide

HRID 2244629Notes

Reaction equation

HRID 2244629 reaction equation
N[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:13](Cl)(=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17].C([N:23](C(C)C)CC)(C)C.O>C1COCC1>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([NH:23][C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17])=[C:9]([N+:10]([O-:12])=[O:11])[CH:2]=1)#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 42284934-Pentenoyl chlorideHCID 15257489HCID 15257489, compound

Product 1

HCID 59214335N-(4-Cyano-2-nitrophenyl)-4-pentenamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-3-nitrobenzonitrile (2 g) in THF (30 ml) were added 4-pentenoyl chloride (2.90 g) and diisopropylethylamine (4.27 ml), followed by stirring at 80° C. for 12 hours. The reaction solution was poured into water, and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:CH3OH) to obtain N-(4-cyano-2-nitrophenyl)pent-4-enamide (174 mg) as a colorless liquid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH)

Sources & evidence

ORD record
ord-917148ad651d4ef591f296c2e07209d8
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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