Hydrazine hydrate (1:1) → 2-Bromo-6-hydrazinopyridine

HRID 2099509Notes

Reaction equation

HRID 2099509 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.O.[NH2:10][NH2:11]>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:10][NH2:11])[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 693532,5-Dibromopyridine

Product 1

HCID 193925882-Bromo-6-hydrazinopyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

2,5-Dibromopyridine (2.0 g, 8.4 mmol) was dissolved in 1,4-dioxane (2 mL) and a solution of hydrazine hydrate (500 mg, 8.4 mmol) in 1,4-dioxane (15 mL) was added dropwise by syringe pump. The reaction was heated to 80° C. for 16 h. The solvents were removed in vaccuo and the residue was chromatographed on silica gel eluting with hexanes:EtOAc (1:1) to afford 2-bromo-6-hydrazinopyridine as a brown solid. MS (ESI) 187.0 (M++H), 189.0 (M+H+2).

Workup

  1. customThe solvents were removed in vaccuo
  2. customthe residue was chromatographed on silica gel eluting with hexanes:EtOAc (1:1)

Sources & evidence

ORD record
ord-604b6f3231b34cc6a36eaec31b9444d1
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

Loading…