2-Nitroaniline → 2-Nitro-(2'-methyl-2'-cyanoethyl)-aniline

HRID 2420229Notes

Reaction equation

HRID 2420229 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:11](#[N:15])[C:12]([CH3:14])=[CH2:13]>O1CCCC1.CO>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][CH2:13][CH:12]([CH3:14])[C:11]#[N:15])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 69462-NitroanilineHCID 31368Methacrylonitrile

Product 1

HCID 124174792-Nitro-(2'-methyl-2'-cyanoethyl)-aniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

69 g (mol/2) of o-nitroaniline in solution in 270 ml of tetrahydrofuran are heated under reflux for 2 hours with 67 g (1 mol) of methacrylonitrile and 16 ml of a 40% solution of "Triton B" in methanol. After evaporation of the volatile substances under vacuum, washing the residue with water and then extraction with ethyl acetate, and after evaporation of the solvent, a yellow solid of melting point 44°-47° C. is obtained in a yield of 51.3 g = 50% (theoretical yield: 102.6 g). After recrystallisation from isopropanol and then from ethanol, there is obtained a yellow product of melting point 75°-76° C.

Workup

  1. customAfter evaporation of the volatile substances under vacuum
  2. washwashing the residue with water
  3. extractionextraction with ethyl acetate
  4. customafter evaporation of the solvent
  5. customa yellow solid of melting point 44°-47° C. is obtained in a yield of 51.3 g = 50% (theoretical yield: 102.6 g)
  6. customAfter recrystallisation from isopropanol
  7. customfrom ethanol, there is obtained a yellow product of melting point 75°-76° C.

Sources & evidence

ORD record
ord-74727acd229645e6bd7e04e696e3ffc6
Source dataset
uspto-grants-1978_08
Patent number
US04110337

Reaction notes

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