Hydrazine hydrate (1:1) → HCID 178487565, compound

HRID 1267293Notes

Reaction equation

HRID 1267293 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=O)[CH3:11].O.[NH2:14][NH2:15]>C(O)CO>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3]([C:10]([CH3:11])=[N:14][NH:15]2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5928212'-Fluoro-4'-methoxyacetophenone

Product 1

HCID 178487565HCID 178487565, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent2×

Conditions

Temperature
165 °C

Procedure

To a stirred solution of 2′-fluoro-4′-methoxyacetophenone (0.5 g, 3.0 mmol) in ethylene glycol (10 mL) was added dropwise hydrazine hydrate (0.1 g, 3.1 mmol). The mixture was stirred for 24 h and partitioned between dichloromethane (20 mL) and water (3×20 mL). The organic layer was dried (magnesium sulfate), concentrated in vacuo and purified by column chromatography [SiO2; ethyl acetate-heptane (1:1)] to give an orange oil. The oil was dissolved in ethylene glycol (10 mL) and heated at 165° C. for 24 h. The solution was cooled to room temperature and partitioned between dichloromethane (20 mL) and water (3×20 mL). The organic extract was dried (magnesium sulfate), concentrated in vacuo and purified by column chromatography [SiO2; ethyl acetate-heptane (1:5)] to give the product (0.25 g, 51%) as a colourless solid: IR νmax (Nujol/cm−1) 1624, 1519, 1458, 1295, 1208, 1170, 1024 and 821; NMR δH (400 MHz, CDCl3) 2.54 (3H, s), 3.86 (3H, s), 6.78-6.81 (2H, m) and 7.52 (1H, d, J 9 Hz).

Workup

  1. custompartitioned between dichloromethane (20 mL) and water (3×20 mL)
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography [SiO2; ethyl acetate-heptane (1:1)]
  5. customto give an orange oil
  6. temperatureThe solution was cooled to room temperature
  7. custompartitioned between dichloromethane (20 mL) and water (3×20 mL)
  8. extractionThe organic extract
  9. dry with materialwas dried (magnesium sulfate)
  10. concentrationconcentrated in vacuo
  11. custompurified by column chromatography [SiO2; ethyl acetate-heptane (1:5)]

Sources & evidence

ORD record
ord-ac959c35e19b4b6fbab85372e1606a0f
Source dataset
uspto-grants-2003_04
Patent number
US06552062B1

Reaction notes

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