Hydrazine → HCID 178478062, compound

HRID 341120Notes

Reaction equation

HRID 341120 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[C:15](F)=[N:14][CH:13]=[CH:12][N:11]=2)=O)[CH:5]=[CH:4][CH:3]=1.[NH2:17][NH2:18]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:10]3[C:15](=[N:14][CH:13]=[CH:12][N:11]=3)[NH:18][N:17]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86677186HCID 86677186, compound

Product 1

HCID 178478062HCID 178478062, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-chloro-2-pyridyl)-(3-fluoropyrazin-2-yl)methanone (1.12 g, 4.713 mmol) in THF (10 mL) was added hydrazine (1M in THF) (9.897 mL of 1 M, 9.897 mmol). Mixture turned orange and an exothermic reaction occurred, cream precipitate rapidly formed and mixture became difficult to stir. Stirred for 45 mins. Added sat. NaHCO3 solution and collected solid by filtration, washing solid with water then petrol. Solid then dried in vacuum oven overnight at 80° C. to leave title compound as an off-white solid (693 mg, 64%). 1H NMR (DMSO-d6) δ 7.58 (d, 1H), 8.07 (t, 1H), 8.52 (d, 1H), 8.70 (d, 1H), 8.80 (d, 1H), 14.55 (br s, 1H). ES+232.13.

Workup

  1. customan exothermic reaction
  2. customcream precipitate rapidly formed
  3. stirringStirred for 45 mins
  4. customAdded sat. NaHCO3 solution and collected solid
  5. filtrationby filtration
  6. washwashing solid with water
  7. customSolid then dried in vacuum oven overnight at 80° C.

Sources & evidence

ORD record
ord-e10b09116b264caea55e9360e5c88e69
Source dataset
uspto-grants-2014_11
Patent number
US08895740B2

Reaction notes

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