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

HRID 383230Notes

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.[CH2:19]([NH2:22])[CH2:20][CH3:21].[CH2:23]=[O:24].[CH2:25](O)C>>[CH2:19]([N:22]1[CH2:25][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][C:11]=2[O:24][CH2:23]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)[CH2:20][CH3:21]

Participants

Reactant 4

HCID 702Ethanol

HCID 712Formaldehyde

HCID 7852Propylamine

HCID 219100Phenoxodiol

Product 1

HCID 250064754-(3-Propyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenolYield 53%

Procedure

4′,7-Dihydroxyisoflav-3-ene (503 mg, 2.09 mmol) was dissolved in ethanol (20 ml). Propylamine (0.25 ml, 3.04 mmol) 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 (362 mg, 53%).

Workup

customThe white precipitate was collected

Sources & evidence

ORD record: ord-40a68c79997744e39b2d993e1e4af37a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367659B2

Reaction notes

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