Hydrochloric Acid → 3-Dimethylamino-2-methyl-4'-chloropropiophenone

HRID 1607206Notes

Reaction equation

HRID 1607206 reaction equation
[CH3:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].Cl.[CH3:13][NH:14][CH3:15].[CH2:16]=O.Cl>C(O)C>[CH3:13][N:14]([CH3:15])[CH2:1][CH:2]([CH3:16])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 226974'-Chloropropiophenone

Product 1

HCID 124144373-Dimethylamino-2-methyl-4'-chloropropiophenone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 500 ml round bottomed flask equipped with a reflux condensor was mixed 84 g of 4-chloropropiophenone (0.50 mole), 50 g of dimethylamine hydrochloride (0.61 mole), 20 g of paraformaldehyde (0.67 mole), 50 ml of ethanol, and 10 ml of concentrated aqueous hydrochloric acid. The mixture was refluxed for 18 hours, cooled and partitioned between ethyl and water. The ether layer was discarded and the aqueous layer was basified with sodium hydroxide and the resulting mixture extracted twice with fresh ethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 105 g of 3-dimethylamino-2-methyl-4'-chloropropiopenone, an oil. NMR data was consistent with the structure.

Workup

  1. customIn a 500 ml round bottomed flask equipped with a reflux condensor
  2. temperatureThe mixture was refluxed for 18 hours
  3. temperaturecooled
  4. custompartitioned between ethyl and water
  5. extractionthe resulting mixture extracted twice with fresh ethyl ether
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto yield 105 g of 3-dimethylamino-2-methyl-4'-chloropropiopenone

Sources & evidence

ORD record
ord-b548c1b1166f435baab4d2598372fa83
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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