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

HRID 892232Notes

Reaction equation

HRID 892232 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 962WaterSolvent

Procedure

A 12 L three-necked round-bottomed flask equipped with a mechanical stirrer and a condenser, connected on top with a nitrogen bubbler and a thermometer, was charged with 2,5-dibromopyridine (442 g, 1.87 moles), hydrazine hydrate (55% wt., 1057 ml, 18.7 moles), poly(ethylene glycol) (average Mn about 300, 1.87 L), 2-butanol (373 ml) and water (1.87 L). The mixture was heated at reflux for 29 hours. The heating source was removed and the mixture was stirred for an additional 20 hours. To the resulting slurry, cold water (2.2 L) was added. The slurry was stirred for an additional 30 minutes and filtered. The cake was washed with cold water (3×200 ml) and dried in a vacuum-oven (40° C.) for 48 hours. The title compound was obtained as off-white flakes (305 g, yield 87%).

Workup

  1. customA 12 L three-necked round-bottomed flask equipped with a mechanical stirrer and a condenser
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 29 hours
  4. customThe heating source was removed
  5. additionTo the resulting slurry, cold water (2.2 L) was added
  6. stirringThe slurry was stirred for an additional 30 minutes
  7. filtrationfiltered
  8. washThe cake was washed with cold water (3×200 ml)
  9. customdried in a vacuum-oven (40° C.) for 48 hours

Sources & evidence

ORD record
ord-3d22c5fdc89448479f93b01dd4dd6520
Source dataset
uspto-grants-2006_02
Patent number
US07005523B2

Reaction notes

Loading…