2-Chloro-4-nitroaniline → HCID 4715112, compound

HRID 2290545Notes

Reaction equation

HRID 2290545 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1>C(O)(=O)C.O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[N:4]1[CH:14]=[CH:18][CH:17]=[CH:16]1

Participants

5

Reactant 2

HCID 84922-Chloro-4-nitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 4715112HCID 4715112, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A stirred mixture of 20.0 g (0.12 mole) of 2-chloro-4-nitroaniline and 17.9 g (0.14 mole) of 2,5-dimethoxytetrahydrofuran in 30 ml of glacial acetic acid was heated at reflux for three hours. The mixture was cooled to room temperature, diluted with water, and extracted with diethyl ether. The extract was washed with a saturated aqueous potassium carbonate solution then dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure to leave a solid. The solid was purified by recrystallization from methylcyclohexane to yield 22.5 g of 1-(2-chloro-4-nitrophenyl)pyrrole (mp 54°-55° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with a saturated aqueous potassium carbonate solution
  5. dry with materialthen dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated from the filtrate under reduced pressure
  8. customto leave a solid
  9. customThe solid was purified by recrystallization from methylcyclohexane

Sources & evidence

ORD record
ord-2e475199f5ac44afba814ec57ad23690
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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