3-Nitroaniline → 3-chloro-N-(3-nitrophenyl)propanamide

HRID 1076933Notes

Reaction equation

HRID 1076933 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[Cl:11][CH2:12][CH2:13][C:14](Cl)=[O:15]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:14](=[O:15])[CH2:13][CH2:12][Cl:11])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74233-NitroanilineHCID 693643-Chloropropionyl chloride

Product 1

HCID 34652363-chloro-N-(3-nitrophenyl)propanamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Nitroaniline (0.3 moles), β-chloropropionyl chloride (0.35 mole) and benzene (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux with stirring for a period of about 4 hours. After this time the reaction mixture is cooled to room temperature and is washed with dilute aqueous sodium bicarbonate, with dilute hydrochloric acid and with water. The washed mixture is then dried over anhydrous magnesium sulfate, filtered and stripped of benzene under reduced pressure to yield the desired product N-(3-nitrophenyl)-β-chloropropionamide as the residue.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux
  5. washis washed with dilute aqueous sodium bicarbonate, with dilute hydrochloric acid and with water
  6. dry with materialThe washed mixture is then dried over anhydrous magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-cebbaf73f2b042388e05a7eb70012b52
Source dataset
uspto-grants-1976_05
Patent number
US03958974

Reaction notes

Loading…