Ethyl Acetate → HCID 19041703, compound

HRID 1684009Notes

Reaction equation

HRID 1684009 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=O)[CH3:10])[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21]N)=[CH:17][CH:16]=1.Cl.O1CCOCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:13][O:14][C:15]1[CH:20]=[C:19]2[C:18](=[CH:17][CH:16]=1)[NH:21][C:9]([CH3:10])=[C:8]2[C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 27340931-(3-Bromophenyl)propan-2-oneHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 19041703HCID 19041703, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The ketone from Step 1 (1.065 g, 5 mmol) and 4-methoxyphenylhydrazine hydrochloride (870 mg, 5 mmol) in toluene (20 is mL) were gently warmed up to 60° C. After 1 h, 4M HCl/dioxane (2 mL) was added and the mixture was heated at 60° C. for 1 h. It was then cooled, poured over ice water and ethyl acetate. The organic layer was separated, washed with dilute NaHCO3. Removal of the solvents left a residue which was purified by chromatography over SiO2 to afford the product (433 mg).

Workup

  1. temperatureIt was then cooled
  2. customThe organic layer was separated
  3. washwashed with dilute NaHCO3
  4. customRemoval of the solvents
  5. waitleft a residue which
  6. customwas purified by chromatography over SiO2

Sources & evidence

ORD record
ord-2c86ea372cef439fba1bc7c3fc5e9a19
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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