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

HRID 552839Notes

Reaction equation

HRID 552839 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-0fa675f5b3334681a4a3804d8f016e8c
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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