Hydrochloric Acid → HCID 54263071, compound

HRID 1732683Notes

Reaction equation

HRID 1732683 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=[O:22])[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])=[CH:8][CH:7]=1)([OH:3])=[O:2].CO[CH:25](OC)[N:26]([CH3:28])[CH3:27].Cl>CN(C)C=O>[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:13](=[O:22])[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:15])=[CH:25][N:26]([CH3:28])[CH3:27])=[CH:8][CH:7]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 78373Dimethylformamide dimethyl acetalHCID 20304500HCID 20304500, compound

Product 1

HCID 54263071HCID 54263071, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.44 g of 3-[4-(2-carboxyethyl)phenyl]-1-phenyl-1,2-propanedione in 25 ml of dry dimethylformamide, cooled in an ice-bath, was added 11 ml of dimethylformamide dimethyl acetal. After stirring at room temperature for 15 min., the reaction mixture was poured onto 300 ml of crushed ice and the reaction mixture was acidified with 25 ml of 1 N hydrochloric acid. The mixture was extracted with methylene chloride. The layers were separated and the organic phase was washed with water, dried, filtered and evaporated under vacuum. Recrystallization of the residue from methylene chloride-ether gave 3.95 g (75%) of 2-[4-(2-carboxyethyl)phenyl]-1-dimethylamino-4-phenyl-1-butene-3,4-dione as yellow crystals after drying at 50° C. for 3 hrs.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. customThe layers were separated
  3. washthe organic phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customRecrystallization of the residue from methylene chloride-ether

Sources & evidence

ORD record
ord-bed5f1d0ec34475894edb6b0c09fc2d5
Source dataset
uspto-grants-1980_12
Patent number
US04238589

Reaction notes

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