Formamide → Isoflavone

HRID 2292122Notes

Reaction equation

HRID 2292122 reaction equation
C([C:8]1[C:9]([OH:30])=[C:10]([C:14]([C:16]2[CH:21]=CC=[C:18]([CH2:22][C:23]3[CH:28]=[CH:27]C=CC=3)[C:17]=2O)=[O:15])[CH:11]=[CH:12][CH:13]=1)C1C=CC=CC=1.C(N)=O>O>[O:30]1[C:9]2[C:10](=[CH:11][CH:12]=[CH:13][CH:8]=2)[C:14](=[O:15])[C:16]([C:17]2[CH:18]=[CH:22][CH:23]=[CH:28][CH:27]=2)=[CH:21]1

Participants

4

Reactant 2

HCID 713FormamideHCID 54413524HCID 54413524, compound

Product 1

HCID 72304IsoflavoneYield 21.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzyl-2-hydroxyphenyl ketone (29.0 g) and formamide (29.0 g). were heated together at 208° for 1 hr. The reaction mixture was cooled and diluted with water. The oily product was extracted into chloroform and the solution washed with water, dried and evaporated. The residue was chromatographed on alumina, eluting with toluene, and the product recrystallised once from petroleum ether (80°-100°) and once from toluene to yield isoflavone (3.55 g), m.pt. 132°-134°

Workup

  1. temperaturewere heated together at 208° for 1 hr
  2. temperatureThe reaction mixture was cooled
  3. extractionThe oily product was extracted into chloroform
  4. washthe solution washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed on alumina
  8. washeluting with toluene
  9. customthe product recrystallised once from petroleum ether (80°-100°) and once from toluene

Sources & evidence

ORD record
ord-31ab96140d294b7084ee00c02ffc6606
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

Loading…