Methylhydrazine → HCID 66614262, compound

HRID 406584Notes

Reaction equation

HRID 406584 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-b1a78c35559448cdbcbd4ffb01284ad7
Source dataset
uspto-grants-2014_06
Patent number
US08754115B2

Reaction notes

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