Hydrazine hydrate (1:1) → 4-Bromo-2-hydrazinylpyridine

HRID 1623986Notes

Reaction equation

HRID 1623986 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](F)[CH:3]=1.O.[NH2:10][NH2:11]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:10][NH2:11])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27628514-Bromo-2-fluoropyridine

Product 1

HCID 534028634-Bromo-2-hydrazinylpyridineYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-bromo-2-fluoropyridine (23.75 g, 135 mmol) in ethanol (120 mL) was added hydrazine monohydrate (65.5 mL, 1350 mmol). The mixture was stirred at 45° C. for 16 h then concentrated. The resulting solid was triturated with water, collected by filtration, rinsed with water, and dried under vacuum, to give the title compound (23.2 g) as a white solid. LCMS m/z=188.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 4.19 (s, 2H), 6.69 (dd, J=5.3, 1.8 Hz, 1H), 6.92 (d, J=1.7 Hz, 1H), 7.69 (s, 1H), 7.84 (d, J=5.3 Hz, 1H).

Workup

  1. concentrationthen concentrated
  2. customThe resulting solid was triturated with water
  3. filtrationcollected by filtration
  4. washrinsed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-474175865309424bab6f68475471bea6
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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