Benzene → 3-Methyl-2-nitro-1,1'-biphenyl

HRID 1995136Notes

Reaction equation

HRID 1995136 reaction equation
N(OCCC(C)C)=O.[CH3:9][C:10]1[C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:14]=[CH:15][CH:16]=1)N.[CH:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCCCCCC>[CH3:9][C:10]1[C:11]([N+:17]([O-:19])=[O:18])=[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 8053Isoamyl NitriteHCID 690383-Methyl-2-nitroaniline

Product 1

HCID 140439853-Methyl-2-nitro-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Procedure

During a two hour period isoamyl nitrite (92.43 g, 0.189 mole) was added to a stirred solution of 3-methyl-2-nitroaniline (60.0 g, 0.394 mole) in 352 ml of benzene. The reaction mixture was stirred at room temperature for approximately 18 hours, then heated at 65° for five hours. The reaction mixture was cooled and the solvent removed by distillation under reduced pressure to give an oil. The oil was diluted with n-heptane and the solvent removed by distillation under reduced pressure to give an oil. The oil was slurried with 100 g silica gel in 300 ml of n-heptane for 15 minutes, then allowed to stand for approximately 18 hours. The slurry was filtered and the filter cake rinsed with toluene. The filtrate was subjected to column chromatography on 500 g of silica gel, elution with toluene:n-heptane (15:85), to give an oil. The oil was rechromatographed on 480 g of silica gel, elution with toluene:n-heptane (15:85), to give 3-methyl-2-nitro-[1,1'-biphenyl].

Workup

  1. temperatureheated at 65° for five hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed by distillation under reduced pressure
  4. customto give an oil
  5. customthe solvent removed by distillation under reduced pressure
  6. customto give an oil
  7. waitto stand for approximately 18 hours
  8. filtrationThe slurry was filtered
  9. washthe filter cake rinsed with toluene
  10. washThe filtrate was subjected to column chromatography on 500 g of silica gel, elution with toluene:n-heptane (15:85)
  11. customto give an oil
  12. customThe oil was rechromatographed on 480 g of silica gel, elution with toluene:n-heptane (15:85)

Sources & evidence

ORD record
ord-29ae458d40cb4ab9bde46cad8a762970
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

Loading…