Dichloromethane → HCID 178434440, compound

HRID 505495Notes

Reaction equation

HRID 505495 reaction equation
F[C:2]1[C:7]([C:8](=O)[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][NH2:12].C(Cl)Cl>C(O)CO>[CH3:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[NH:12][N:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 127111221-(2-Fluoropyridin-3-yl)ethan-1-one

Product 1

HCID 178434440HCID 178434440, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A stirred solution of 1.10 g (7.91 mmol) of 1-(2-fluoropyridine-3-yl)ethanone in 5 mL of ethylene glycol under nitrogen was treated with 265 μL (8.31 mmol) of hydrazine. This solution was stirred for 2 hours at room temperature and then heated at 165° C. for 1.5 hours. The solution was cooled to room temperature, poured into CH2Cl2 (25 mL), and extracted with H2O (2×50 mL). The organic portions were combined, dried (MgSO4), filtered and concentrated in vacuo to give the title product as a fluffy off-white solid. 1H NMR (CDCl3): δ 2.61 (s, 3H), 7.14 (m, 1H), 8.06 (dd, 1H), 8.58 (dd, 1H), 11.18 (br s, 1H).

Workup

  1. temperatureheated at 165° C. for 1.5 hours
  2. temperatureThe solution was cooled to room temperature
  3. extractionextracted with H2O (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed6de7a7d05a4ecd919cfda6725f7778
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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