4-Chloro-2-nitroaniline → HCID 10846711, compound

HRID 1578690Notes

Reaction equation

HRID 1578690 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1>C(O)(=O)C>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([N:15]2[CH:3]=[CH:7][CH:6]=[CH:5]2)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1

Participants

4

Reactant 2

HCID 69794-Chloro-2-nitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 10846711HCID 10846711, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

100 g (0.75 mole) of 2,5-dimethoxytetrahydrofuran are added dropwise to a stirred solution of 86.3 g (0.5 mole) of 4-chloro-2-nitroaniline in 500 ml. of glacial acetic acid. The solution is refluxed under a nitrogen atmosphere for 30 minutes, filtered, and poured into 2500 ml. of water. The aqueous solution is extracted with chloroform. The chloroform solution is dried with anhydrous sodium sulfate and concentrated to a brown oil. The brown oil is dissolved in an ether-petroleum ether-mixture and placed in a refrigerator overnight. An orange solid precipitates and is recrystallized from an ether petroleum ether mixture to give 1-(4-chloro-2-nitrophenyl) pyrrole, m.p. 55°-56° C.

Workup

  1. temperatureThe solution is refluxed under a nitrogen atmosphere for 30 minutes
  2. filtrationfiltered
  3. additionpoured into 2500 ml
  4. extractionThe aqueous solution is extracted with chloroform
  5. dry with materialThe chloroform solution is dried with anhydrous sodium sulfate
  6. concentrationconcentrated to a brown oil
  7. dissolutionThe brown oil is dissolved in an ether-petroleum ether-mixture
  8. customplaced in a refrigerator overnight
  9. customAn orange solid precipitates
  10. customis recrystallized from an ether petroleum ether mixture

Sources & evidence

ORD record
ord-491cab11651046f7aa76d2fcd23eeb2d
Source dataset
uspto-grants-1976_02
Patent number
US03939159

Reaction notes

Loading…