Sodium Hydroxide → 4-Bromo-2-hydrazinylpyridine

HRID 879568Notes

Reaction equation

HRID 879568 reaction equation
O.[NH2:2][NH2:3].[Br:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7](F)[CH:6]=1.[OH-].[Na+]>O>[Br:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:2][NH2:3])[CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 27628514-Bromo-2-fluoropyridine

Product 1

HCID 534028634-Bromo-2-hydrazinylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring solution of hydrazine monohydrate (16 mL) was added 4-bromo-2-fluoropyridine (3.4 mL, 33.1 mmol). After stirring for 23 hours at room temperature, 4M NaOH (15 mL) and water (30 mL) were added, and the thick suspension was stirred vigorously for 15 minutes. The precipitated solids were filtered off and dried to give the product. 1H NMR (400 MHz, CDCl3) δ 7.91 (d, J=5.4 Hz, 1H), 6.97 (d, J=1.3 Hz, 1H), 6.80 (dd, J=5.4, 1.5 Hz, 1H), 6.05 (br s, 1H), 3.65 (br s, 2H).

Workup

  1. stirringthe thick suspension was stirred vigorously for 15 minutes
  2. filtrationThe precipitated solids were filtered off
  3. customdried
  4. customto give the product

Sources & evidence

ORD record
ord-943fb7a3835c40f09d110b5af6e30a70
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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