Reaction #470423

ord-4db3b4f51a0143e7987a2571c2824bf5

Reaction equation

Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
4′,7-Dihydroxyisoflav-3-ene
Nc1cccc([N+](=O)[O-])c1
3-nitroaniline
CCO
ethanol
C=O
Formaldehyde
O=[N+]([O-])c1cccc(N2COc3cc4c(cc3C2)C=C(c2ccc(O)cc2)CO4)c1
title compound
Yield 4.0%
O=[N+]([O-])c1cccc(N2COc3cc4c(cc3C2)C=C(c2ccc(O)cc2)CO4)c1
4-(3-(3-Nitrophenyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol
Yield 4.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe resulting precipitate was collected

Procedure

4′,7-Dihydroxyisoflav-3-ene (527 mg, 2.19 mmol) and 3-nitroaniline (333 mg, 2.41 mmol) were dissolved in ethanol (8 ml). Formaldehyde solution (2 ml, 0.03 mol, 37% wt) was added and the reaction stirred at room temperature for 3 days. The resulting precipitate was collected to afford the title compound (35 mg, 4%).

Source

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