Hydrochloric Acid → HCID 13408303, compound

HRID 1035595Notes

Reaction equation

HRID 1035595 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CN(C)C1C=CC=CC=1.CO[C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH2:29]Br)=O)=[CH:23][CH:22]=1.Cl.[C:32](OCC)(=[O:34])C>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:27]([C:24]1[CH:23]=[CH:22][CH:21]=[C:26]([O:34][CH3:32])[CH:25]=1)=[CH:29]2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 7732P-AnisidineHCID 8857Ethyl Acetate2×

Product 1

HCID 13408303HCID 13408303, compoundYield 15%

Conditions

Temperature
180 °C

Procedure

To a boiling mixture of p-anisidine (2.46 g, 20 mmol, 6.66 eq) and N,N-dimethylaniline (3.5 ml) is slowly added dropwise 2-bromo-4-methoxyacetophenone (0.7 g, 3 mmol, 1 eq) dissolved in ethyl acetate (12 ml). After the addition is complete, the reaction mixture is stirred at 180° C. for 2 h. To the cooled mixture are added ethyl acetate and 2 M HCl. The aqueous phase is extracted with ethyl acetate several times, and the combined organic phases are washed with a saturated NaCl solution, dried over MgSO4, filtered and evaporated to dryness on a rotary evaporator. Purification by column chromatography (eluent dichloromethane/hexane 7/3) yields the desired product in a yield of 15% (760 mg).

Workup

  1. additionAfter the addition
  2. extractionThe aqueous phase is extracted with ethyl acetate several times
  3. washthe combined organic phases are washed with a saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness on a rotary evaporator
  7. customPurification by column chromatography (eluent dichloromethane/hexane 7/3)

Sources & evidence

ORD record
ord-e7396f0c557e432c8b441600ac1c183b
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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