Hydrazine hydrate (1:1) → 2-Hydrazinyl-4-(phenylmethoxy)-3-(trifluoromethyl)pyridine

HRID 1841967Notes

Reaction equation

HRID 1841967 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](Cl)[C:10]=1[C:16]([F:19])([F:18])[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:21][NH2:22]>O1CCOCC1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:21][NH2:22])[C:10]=1[C:16]([F:19])([F:18])[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57459601HCID 57459601, compound

Product 1

HCID 574596022-Hydrazinyl-4-(phenylmethoxy)-3-(trifluoromethyl)pyridineYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a suspension of compound D7 (1.09 g g, 3.789 mmol) in 1,4-dioxane (9 ml), was added hydrazine monohydrate (3.676 ml, 75.78 mmol). The reaction mixture was heated at 160° C. under microwave irradiation for 30 min. After cooling the resulting solution was concentrated in vacuo. The residue thus obtained was dissolved in DCM and washed with NaHCO3 (aqueous sat. solution). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to yield intermediate compound D8 (0.890 g, 83%) as a white solid.

Workup

  1. temperatureAfter cooling the resulting solution
  2. concentrationwas concentrated in vacuo
  3. customThe residue thus obtained
  4. washwashed with NaHCO3 (aqueous sat. solution)
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9084d418f04486bb8a6abbfe65b1c91
Source dataset
uspto-grants-2015_02
Patent number
US08946205B2

Reaction notes

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