Hydrochloric Acid → 5-Fluoro-2-hydrazinyl-3-methylpyridine

HRID 2285170Notes

Reaction equation

HRID 2285170 reaction equation
C(=[N:14][NH:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([F:23])=[CH:18][N:17]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C1(C)C=CC=CC=1.O>[F:23][C:19]1[CH:20]=[C:21]([CH3:22])[C:16]([NH:15][NH2:14])=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86687171N-Benzhydrylidene-N'-(5-fluoro-3-methyl-pyridin-2-yl)-hydrazine

Product 1

HCID 534030065-Fluoro-2-hydrazinyl-3-methylpyridineYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of Intermediate 105a (194 mg, 0.635 mmol) in toluene (13 mL) was treated with HCl (37%, 3.5 mL) and heated at 110° C. for 1.5 h. After cooling to RT, the reaction mixture was diluted with water and extracted with toluene (×3). The aqueous layer was cooled to 0° C., neutralised with 5N NaOH and extracted with DCM (×3). The combined organic layers were dried (MgSO4) and concentrated in vacuo to afford the title compound (78 mg, 86%) as a silver/green solid. LCMS (Method 4): Rt 0.29 min, m/z 142 [MH+].

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with toluene (×3)
  3. temperatureThe aqueous layer was cooled to 0° C.
  4. extractionextracted with DCM (×3)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d9e6f6eb29b41479a178cfa1f17105f
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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