Hydrazine hydrate (1:1) → HCID 178434364, compound

HRID 1412092Notes

Reaction equation

HRID 1412092 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH3:9])[C:5](F)=[CH:4][N:3]=1.O.[NH2:13][NH2:14]>C(O)CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:8]([CH3:9])=[N:14][NH:13][C:5]2=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 252229461-(2-Bromo-5-fluoropyridin-4-yl)ethan-1-one

Product 1

HCID 178434364HCID 178434364, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
165 °C

Procedure

To a 250-mL round-bottomed flask equipped with a reflux condenser was added dry ethylene glycol (30 mL) and 325c (4.3 g, 20 mmol). Then hydrazine hydrate (5.0 mL, 4.8 g, 81.6 mmol) was added dropwise via a syringe. The mixture was heated at 165° C. for 3.5 h. The resulting orange-tan mixture was cooled to room temperature and the contents were poured onto a stirring mixture of 100 mL ice/water (1:1), whereupon precipitation occurred. After stirring for 10 min, the off-white precipitate was collected, which was dried in vacuo to afford 325d as an off-white solid (3.1 g, 74%). MS-ESI: [M+H]+ 211.9.

Workup

  1. customTo a 250-mL round-bottomed flask equipped with a reflux condenser
  2. temperatureThe resulting orange-tan mixture was cooled to room temperature
  3. customthe off-white precipitate was collected
  4. customwhich was dried in vacuo

Sources & evidence

ORD record
ord-33a6a791a9b149d1a492e2cd95b1e680
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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