Hydrazine → 2-Bromo-6-hydrazinopyridine

HRID 882012Notes

Reaction equation

HRID 882012 reaction equation
[NH2:1][NH2:2].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[N:5]=1>O>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:1][NH2:2])[N:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 122742,6-Dibromopyridine

Product 1

HCID 193925882-Bromo-6-hydrazinopyridineYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Hydrazine (27 mL, 83 mmol) was added to 2,6-dibromopyridine (20 g, 84 mmol), and the resulting suspension was heated at 70° C. for 30 min. The solution was cooled to 50° C. and diluted with H2O (150 mL). The resulting solids were stirred for 2 h, collected by filtration, and washed with H2O (350 mL) to provide the title compound (13 g, 83%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 7.87 (s, 1H), 7.34 (overlapping dd, J=7.8 Hz, 1H), 6.68 (d, J=7.8 Hz, 1H), 6.65 (d, J=7.8 Hz, 1H), 4.19 (s, 2H).

Workup

  1. temperatureThe solution was cooled to 50° C.
  2. filtrationcollected by filtration
  3. washwashed with H2O (350 mL)

Sources & evidence

ORD record
ord-54b7a2794f6d409fb7a20a0c246ae946
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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