Reaction #470414

ord-362ac1f0e9d243b38923552245386a46

Reaction equation

Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
4′,7-Dihydroxyisoflav-3-ene
CCO
ethanol
Nc1ccccc1
Aniline
C=O
formaldehyde
Oc1ccc(C2=Cc3cc4c(cc3OC2)OCN(c2ccccc2)C4)cc1
title compound
Yield 7.0%
Oc1ccc(C2=Cc3cc4c(cc3OC2)OCN(c2ccccc2)C4)cc1
4-(3-Phenyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol
Yield 7.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe white precipitate was collected

Procedure

4′,7-Dihydroxyisoflav-3-ene (501 mg, 2.09 mmol) was dissolved in ethanol (15 ml). Aniline (0.25 ml, 2.74 mmol) was added followed by formaldehyde solution (2 ml, 0.03 mol, 37% wt.). The reaction was stirred at room temperature for 3 days. The white precipitate was collected to afford the title compound (53 mg, 7%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08367659B2uspto-grants-2013_02