Hydrazine hydrate (1:1) → 3-(3,5-Dibromobenzyl)pyridine

HRID 725027Notes

Reaction equation

HRID 725027 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Br:16])[CH:15]=1)[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.O.NN>C(O)CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Br:16])[CH:15]=1)[CH2:5][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 106649193-(3,5-Dibromobenzoyl)pyridine

Product 1

HCID 106639243-(3,5-Dibromobenzyl)pyridine

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-(3,5-dibromobenzoyl)pyridine (Preparation 1; 19.0 g) and hydrazine hydrate (13.9 ml) in ethylene glycol (140 ml) was heated under reflux for 45 minutes. The volatile material was distilled off until the internal temperature reached 180° C, and then the reaction mixture was cooled to 80° C. Potassium hydroxide (7.80 g) was added and the resulting solution was heated under reflux for 30 minutes, cooled and then poured into water. The mixture was extracted several times with ethyl acetate, and the combined extracts were washed with water and dried (MgSO4). Evaporation under vacuum gave the title compound (16.38 g), m.p. 70°-72° C. (after crystallisation from ethyl acetate-hexane). Found: C, 44.29; H, 2.66; N, 4.29. C12H9 Br2N requires C, 44.07; H, 2.77; N, 4.28%.

Workup

  1. temperatureunder reflux for 45 minutes
  2. distillationThe volatile material was distilled off until the internal temperature
  3. customreached 180° C
  4. additionPotassium hydroxide (7.80 g) was added
  5. temperaturethe resulting solution was heated
  6. temperatureunder reflux for 30 minutes
  7. temperaturecooled
  8. additionpoured into water
  9. extractionThe mixture was extracted several times with ethyl acetate
  10. washthe combined extracts were washed with water
  11. dry with materialdried (MgSO4)
  12. customEvaporation under vacuum
  13. customgave
  14. customthe title compound (16.38 g), m.p. 70°-72° C. (after crystallisation from ethyl acetate-hexane)

Sources & evidence

ORD record
ord-5e3fc040201a455f865f168bd085d66a
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

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