Ethanol → 4-(3-Phenyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

HRID 383232Notes

Reaction equation

HRID 383232 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][CH:23]=[CH:22][CH:21]=1.[CH2:26]=[O:27].[CH2:28](O)C>>[C:20]1([N:19]2[CH2:28][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][C:11]=3[O:27][CH2:26]2)[O:8][CH2:7][C:6]([C:5]2[CH:17]=[CH:18][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:15]4)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 6115AnilineHCID 219100Phenoxodiol

Product 1

HCID 250064794-(3-Phenyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenolYield 7%

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%).

Workup

  1. customThe white precipitate was collected

Sources & evidence

ORD record
ord-362ac1f0e9d243b38923552245386a46
Source dataset
uspto-grants-2013_02
Patent number
US08367659B2

Reaction notes

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