Methylhydrazine → HCID 66614262, compound

HRID 2276014Notes

Reaction equation

HRID 2276014 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6](=O)[CH3:7].CO[CH:16](OC)[N:17]([CH3:19])C.C[NH:23]N>C(O)(=O)C>[Cl:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][C:5]1[C:6]([CH3:7])=[N:23][N:17]([CH3:19])[CH:16]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 606245511-(2-Chloro-4-fluorophenoxy)-2-propanone2×

Product 1

HCID 66614262HCID 66614262, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(2-chloro-4-fluorophenoxy)-2-propanone (i.e. the product of Step A) (1.40 g, 6.93 mmol) and N,N-dimethylformamide dimethyl acetal (1.38 mL, 10.4 mmol) was heated to 90° C. for 3 h, and then concentrated under reduced pressure. The resulting material was diluted with ethanol (15 mL), and then methylhydrazine (0.49 mL, 9.0 mmol) and acetic acid (0.1 mL) were added. After 15 h, the reaction mixture was concentrated under reduced pressure and the resulting material was purified by silica gel column chromatography (5 to 40% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a brown yellow oil (680 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting material was diluted with ethanol (15 mL)
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe resulting material was purified by silica gel column chromatography (5 to 40% gradient of ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-ef91a5a5e9a4463c8aa57d265d7772e5
Source dataset
uspto-grants-2015_09
Patent number
US09131693B2

Reaction notes

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