Hydrochloric Acid → HCID 53897224, compound

HRID 2165086Notes

Reaction equation

HRID 2165086 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[C:16]([NH:17][C:18](=[O:32])[CH:19]=[CH:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:22]=3)=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1)=[O:5])C.C(O)C.C(=O)(O)[O-].[Na+].Cl>O>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([CH:20]=[CH:19][C:18]([NH:17][C:16]2[C:8]3[O:7][C:6]([C:4]([OH:5])=[O:3])=[CH:11][C:10](=[O:12])[C:9]=3[CH:13]=[CH:14][CH:15]=2)=[O:32])=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 54225327HCID 54225327, compound

Product 1

HCID 53897224HCID 53897224, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-(p-pentylcinnamoyl)amino-4-oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester (132 mg; synthesized in example 3) was dissolved into ethanol (10 ml). To the solution, an aqueous solution (1 ml) of sodium bicarbonate (126 mg) was added. The mixture was refluxed for 15 min. To the reaction solution mixture cooled to room temperature, water (20 ml) and 1N hydrochloric acid (2 ml) were added. The mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried, and concentrated under reduced pressure. The residue was washed with a mixture of ethyl acetate and hexane (1:1), and dried to give the title compound (62 mg) having the following physical data:

Workup

  1. temperatureThe mixture was refluxed for 15 min
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with a mixture of ethyl acetate and hexane (1:1)
  7. customdried

Sources & evidence

ORD record
ord-a9c9c7a9ac774738b6921c71ee6b2ae4
Source dataset
uspto-grants-1990_07
Patent number
US04939141

Reaction notes

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