Hydrazine hydrate (1:1) → 4-Bromo-2-[(1Z)-1-hydrazinylideneethyl]pyridine

HRID 879575Notes

Reaction equation

HRID 879575 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=O)[CH3:9])[CH:3]=1.O.[NH2:12][NH2:13]>CO>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](/[C:8](=[N:12]\[NH2:13])/[CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 234370521-(4-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 898605244-Bromo-2-[(1Z)-1-hydrazinylideneethyl]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 1-(4-bromopyridin-2-yl)ethanone (2.4 g, 12 mmol) in MeOH (40 mL) was added hydrazine monohydrate (2.9 mL, 60 mmol) in one portion. After stirring at room temperature for 2 hours, the mixture was concentrated to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.34 (d, J=5.3 Hz, 1H), 8.14 (d, J=1.8 Hz, 1H), 7.33 (dd, J=5.3, 1.8 Hz, 1H), 5.66 (br s, 2H), 2.23 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated
  2. customto afford the product

Sources & evidence

ORD record
ord-5a619f4be4f4477b849719ddeb27d596
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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