Ethylenediamine → HCID 21463158, compound

HRID 1940979Notes

Reaction equation

HRID 1940979 reaction equation
O=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([C:18]([OH:20])=O)[O:3]1.[CH2:21]([NH2:24])[CH2:22][NH2:23]>>[O:20]=[C:18]1[C:4]2[N:24]([C:2](=[O:3])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[C:5]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:21][CH2:22][NH:23]1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 42017421-oxo-4-phenyl-1H-isochromene-3-carboxylic acid

Product 1

HCID 21463158HCID 21463158, compound

Procedure

A mixture of 1-oxo-4-phenyl-1H-2-benzopyran-3-carboxylic acid (500 mg) and ethylenediamine (15 ml) was stirred at room temperature overnight. After evaporation of the solvent, concentrated hydrochloric acid (10 ml) and acetic acid (10 ml) were added to the residue. The mixture was heated under reflux for 48 hours. To the mixture was added water, and extracted with ethyl acetate. The extract was washed successively with water, aqueous sodium hydrogen carbonate and water, dried, and evaporated to yield the title compound as colorless crystals (115 mg).

Workup

  1. customAfter evaporation of the solvent, concentrated hydrochloric acid (10 ml) and acetic acid (10 ml)
  2. additionwere added to the residue
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 48 hours
  5. additionTo the mixture was added water
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed successively with water, aqueous sodium hydrogen carbonate and water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-ea8907fe1ee34b42b5b4d859cd674457
Source dataset
uspto-grants-1997_12
Patent number
US05700810

Reaction notes

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