4-Aminophenol → 4,4'-(Chromeno[6,7-e][1,3]oxazine-3,7(2H,4H,8H)-diyl)diphenol

HRID 383233Notes

Reaction equation

HRID 383233 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[CH2:7][O:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11](O)[CH:10]=3)=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.[CH2:27]=[O:28].[CH2:29](O)C>>[O:28]1[C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][C:12]=2[CH2:29][N:19]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH2:27]1)[CH:15]=[C:6]([C:5]1[CH:17]=[CH:18][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:7][O:8]3

Participants

5

Reactant 4

HCID 4034-AminophenolHCID 702EthanolHCID 712FormaldehydeHCID 219100Phenoxodiol

Product 1

HCID 250022354,4'-(Chromeno[6,7-e][1,3]oxazine-3,7(2H,4H,8H)-diyl)diphenolYield 79%

Procedure

4′,7-Dihydroxyisoflav-3-ene (509 mg, 2.12 mmol) and 4-aminophenol (307 mg, 2.81 mmol) were dissolved in ethanol (15 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 (178 mg, 79%).

Workup

  1. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-7d2f27b2941b40d4b36aff48e8e8e096
Source dataset
uspto-grants-2013_02
Patent number
US08367659B2

Reaction notes

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