4-Nitroaniline → N-(4-nitrophenyl)butanamide

HRID 1375286Notes

Reaction equation

HRID 1375286 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].CN1CCOCC1.[C:18](Cl)(=[O:22])[CH2:19][CH2:20][CH3:21]>C(Cl)Cl>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:18](=[O:22])[CH2:19][CH2:20][CH3:21])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 79724-MethylmorpholineHCID 8855Butyryl chloride

Product 1

HCID 346259N-(4-nitrophenyl)butanamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-nitro aniline (1.01 g, 7.23 mmol) in anhydrous CH2Cl2 (20 mL) was added NMM (0.95 mL, 8.68 mmol). To the reaction mixture was added dropwise butyryl chloride (1.00 mL, 8.68 mmol) at 0° C. After stirring for 0.5 h, the reaction was extracted with CH2Cl2 (20 mL), washed with H2O (30 mL), dried over Na2SO4, and evaporated in vacuo to give N-(4-Nitrophenyl)butyramide (1.50 g, 100%) as a white solid.

Workup

  1. extractionthe reaction was extracted with CH2Cl2 (20 mL)
  2. washwashed with H2O (30 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b338941525c444359085adba3475575b
Source dataset
uspto-grants-2007_01
Patent number
US07166744B2

Reaction notes

Loading…