Nitric Acid → 2-[2-(4-Bromo-2-nitrophenyl)propyl]pyridine

HRID 1579373Notes

Reaction equation

HRID 1579373 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1.[N+:17]([O-])([OH:19])=[O:18]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 205600682-[2-(4-Bromophenyl)propyl]pyridine

Product 1

HCID 205599842-[2-(4-Bromo-2-nitrophenyl)propyl]pyridine

Procedure

2-(p-Bromophenyl)-1-(2-pyridyl)propane (11.5 g., 0.043 mole) is heated in 80 ml. of concentrated nitric acid (specific gravity 1.42, 69-71%) for 4.5 hr. at 80°C. The solution is cooled, quenched in 300 g. of ice, made alkaline with sodium hydroxide, and extracted with ethyl acetate. The extract washed with water and brine, dried over sodium sulfate, and evaporated affords 12.2 g. (88%) of oily nitrated product of sufficient purity to be used in following "step d". Distillation provides analytically pure 2-(4-bromo-2-nitrophenyl)-1-(2-pyridyl)propane, b.p. 172°-176°C. (0.2 mm. Hg.), nD 29 1.5968.

Workup

  1. customat 80°C
  2. temperatureThe solution is cooled
  3. customquenched in 300 g
  4. extractionextracted with ethyl acetate
  5. washThe extract washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customaffords 12.2 g
  9. distillationDistillation

Sources & evidence

ORD record
ord-1a8517b4380147248f070ec961b5d6a1
Source dataset
uspto-grants-1976_01
Patent number
US03931195

Reaction notes

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