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

HRID 854428Notes

Reaction equation

HRID 854428 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 then cooled and stirred for 20 hours. To the resulting slurry, cold water (220 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%) is obtained as off-white flakes.

Workup

  1. temperatureis refluxed gently for 29 hours
  2. temperatureThe mixture is then 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-a2d26b2b446c41998259384037df82c0
Source dataset
uspto-grants-2007_08
Patent number
US07259171B2

Reaction notes

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