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

HRID 383231Notes

Reaction equation

HRID 383231 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.[CH3:19][NH2:20].[CH2:21]=[O:22].[CH2:23](O)C>>[CH3:19][N:20]1[CH2:23][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][C:11]=2[O:22][CH2:21]1)[O:8][CH2:7][C:6]([C:5]1[CH:17]=[CH:18][C:2]([OH:1])=[CH:3][CH:4]=1)=[CH:15]3

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 6329MethylamineHCID 219100Phenoxodiol

Product 1

HCID 250064764-(3-Methyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenolYield 79%

Procedure

4′,7-Dihydroxyisoflav-3-ene (507 mg, 2.11 mmol) was dissolved in ethanol (20 ml). Methylamine solution (0.6 ml, 4.82 mmol, 33% wt. in ethanol) was added followed by formaldehyde solution (2 ml, 0.03 mol, 37% wt.). The reaction was stirred at room temperature for 1 day. The white precipitate was collected to afford the title compound (490 mg, 79%).

Workup

  1. customThe white precipitate was collected

Sources & evidence

ORD record
ord-2f02980a2e2e4923a88b1054c1a814e9
Source dataset
uspto-grants-2013_02
Patent number
US08367659B2

Reaction notes

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