(+-)-2-Butanol → 5-Bromo-2-hydrazinopyridine

HRID 854435Notes

Reaction equation

HRID 854435 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.O.[NH2:10][NH2:11].CC(O)CC>O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:10][NH2:11])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 6568(+-)-2-ButanolHCID 24654Hydrazine hydrate (1:1)HCID 693532,5-Dibromopyridine

Product 1

HCID 115356995-Bromo-2-hydrazinopyridineYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2,5-dibromopyridine (44.2 g, 0.187 moles), hydrazine hydrate (55% by weight, 105.7 mL, 1.87 mol), poly(ethylene glycol) (187.0 mL), 2-butanol (37.3 mL) and water (187.0 mL) under nitrogen is refluxed gently for 29 hours. The mixture is cooled and stirred for 20 hours. To the resulting slurry, cold water (220.0 mL) is added. The slurry is stirred for an additional 30 minutes and filtered. The cake is washed with cold water (3×) and dried in a vacuum-oven (40-45° C.) for 48 hours. The title compound (30.5 g, 87%) may be obtained as off-white flakes.

Workup

  1. temperatureis refluxed gently for 29 hours
  2. temperatureThe mixture is cooled
  3. stirringThe slurry is stirred for an additional 30 minutes
  4. filtrationfiltered
  5. washThe cake is washed with cold water (3×)
  6. customdried in a vacuum-oven (40-45° C.) for 48 hours

Sources & evidence

ORD record
ord-f390d135d91444799f1f438cf1d9a24a
Source dataset
uspto-grants-2007_08
Patent number
US07259171B2

Reaction notes

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