Hydrochloric Acid → 2-(4-Carboxyphenyl)-1-dimethylamino-4-phenyl-1-butene-3,4-dione

HRID 1732689Notes

Reaction equation

HRID 1732689 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:20])[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].CO[CH:23](OC)[N:24]([CH3:26])[CH3:25].Cl.O>CN(C)C=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:11](=[O:20])[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:23][N:24]([CH3:26])[CH3:25])=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 20304493HCID 20304493, compound

Product 1

HCID 540610692-(4-Carboxyphenyl)-1-dimethylamino-4-phenyl-1-butene-3,4-dioneYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-carboxyphenyl)-1-phenyl-1,2-propanedione in 100 ml of dry dimethylformamide cooled in an ice-bath was added, with stirring, 56 ml of dimethylformamide dimethyl acetal. The reaction mixture was stirred at 0°-5° C. for 10 min. and then it was poured onto 1.2 l of ice-water and acidified with 130 ml of 1 N hydrochloric acid. After stirring for 5 min., 1.8 l of water was added and the precipitate was collected, washed with water and air-dried. The filter cake was dissolved in 1.7 l of methylene chloride, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to about 200 ml. Ether (200 ml) was added and the solution was concentrated to about 300 ml and allowed to stand at room temperature for 2 days. The solid was collected, washed with methylene chloride-ether (1:9) and dried at 80° C. for 3 hrs. to give 17.4 g (44%) of 2-(4-carboxyphenyl)-1-dimethylamino-4-phenyl-1-butene-3,4-dione as yellow crystals, m.p. 208°-209° C.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at 0°-5° C. for 10 min.
  3. stirringAfter stirring for 5 min.
  4. customthe precipitate was collected
  5. washwashed with water
  6. customair-dried
  7. dissolutionThe filter cake was dissolved in 1.7 l of methylene chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated to about 200 ml
  11. additionEther (200 ml) was added
  12. concentrationthe solution was concentrated to about 300 ml
  13. customThe solid was collected
  14. washwashed with methylene chloride-ether (1:9)
  15. customdried at 80° C. for 3 hrs

Sources & evidence

ORD record
ord-f617c73aeffd4550b74e99cf11f8ef5f
Source dataset
uspto-grants-1980_12
Patent number
US04238589

Reaction notes

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