2-Methoxy-4-nitroaniline → HCID 880985, compound

HRID 2290556Notes

Reaction equation

HRID 2290556 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[CH2:13]([CH2:17][C:18](=O)[CH3:19])[C:14]([CH3:16])=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:19][C:18]1[N:5]([C:4]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:3]=2[O:2][CH3:1])[C:14]([CH3:16])=[CH:13][CH:17]=1

Participants

5

Reactant 2

HCID 73372-Methoxy-4-nitroanilineHCID 80352,5-Hexanedione

Product 1

HCID 880985HCID 880985, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A stirred mixture of 29.0 g (0.17 mole) of 2-methoxy-4-nitroaniline, 18.7 g (0.16 mole) of acetonylacetone and 0.5 g (0.0026 mole) of p-toluenesulfonic acid in 300 ml of toluene was heated at reflux for two hours. A Dean-Stark trap was used to collect a calculated volume of water. The reaction mixture was cooled then poured into 250 ml of ice water. To the mixture was added 100 ml 2N hydrochloric acid. The organic phase was separated and washed in succession with 100 ml of 2N hydrochloric acid, 100 ml of saturated aqueous sodium chloride, 100 ml of 5% aqueous sodium bicarbonate and 100 ml of saturated aqueous sodium chloride. The washed organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure to yield 39.1 g of 2,5-dimethyl-1-(2-methoxy-4-nitrophenyl)pyrrole.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. customto collect a calculated volume of water
  4. temperatureThe reaction mixture was cooled
  5. additionthen poured into 250 ml of ice water
  6. additionTo the mixture was added 100 ml 2N hydrochloric acid
  7. customThe organic phase was separated
  8. washwashed in succession with 100 ml of 2N hydrochloric acid, 100 ml of saturated aqueous sodium chloride, 100 ml of 5% aqueous sodium bicarbonate and 100 ml of saturated aqueous sodium chloride
  9. dry with materialThe washed organic phase was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-50b4283232be4b14a2e5ddf1d38ad85d
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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