2-Methyl-4-nitroaniline → N-(2-Methyl-4-nitrophenyl)-3,4-dihydro-2H-pyrrol-5-amine

HRID 484785

Reaction equation

HRID 484785 reaction equation
Cl[C:2]1[CH2:6][CH2:5][CH2:4][N:3]=1.[CH3:7][C:8]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:9]=1[NH2:10]>C(#N)C>[CH3:7][C:8]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:9]=1[NH:10][C:2]1[CH2:6][CH2:5][CH2:4][N:3]=1

Participants

4

Reactant 2

HCID 74412-Methyl-4-nitroanilineHCID 135201412-Chloro-1-pyrroline

Product 1

HCID 13520142N-(2-Methyl-4-nitrophenyl)-3,4-dihydro-2H-pyrrol-5-amineYield 51.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-1-pyrroline (1.2 mole), prepared as in Example 1, and 91.3 g (0.6 mole) of 2-methyl-4-nitroaniline were heated at reflux in 900 ml of acetonitrile for two hours. The solid obtained by cooling and filtering was combined with that obtained by concentrating the filtrate to dryness, then dissolved in hot water and filtered. The solution was cooled and washed with ethyl acetate, and the aqueous phase was made basic with 4 N sodium hydroxide. The crude product was extracted into dichloromethane, which was then removed in vacuo. The resultant solid was washed repeatedly with diethyl ether to give 67.7 g of pure title compound. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. temperaturewere heated
  2. customThe solid obtained
  3. temperatureby cooling
  4. filtrationfiltering
  5. customthat obtained
  6. concentrationby concentrating the filtrate to dryness
  7. dissolutiondissolved in hot water
  8. filtrationfiltered
  9. temperatureThe solution was cooled
  10. washwashed with ethyl acetate
  11. extractionThe crude product was extracted into dichloromethane, which
  12. customwas then removed in vacuo
  13. washThe resultant solid was washed repeatedly with diethyl ether

Sources & evidence

ORD record
ord-51e1a3db10db46469f4db076b15c57ae
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Linked notes

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