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

HRID 892238Notes

Reaction equation

HRID 892238 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 mol), 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 was refluxed gently for 29 hours. The mixture was cooled and stirred for 20 hours. To the resulting slurry, cold water (220.0 mL) was added. The slurry was stirred for an additional 30 minutes and filtered. The cake was washed with cold water (3×) and dried in a vacuum-oven (40–45° C.) for 48 hours. The title compound (30.5 g, 87%) was obtained as off-white flakes.

Workup

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

Sources & evidence

ORD record
ord-3306bb7303a749058bd1413df0bfc462
Source dataset
uspto-grants-2006_02
Patent number
US07005523B2

Reaction notes

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