Morpholine → 7-Hydroxyisoflavone

HRID 1741272Notes

Reaction equation

HRID 1741272 reaction equation
OC1C=C(O)C=CC=1C([C:16]([CH:18]([C:25]1C=CC(O)=CC=1O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17])C1C=CC=CC=1.N1[CH2:38][CH2:37][O:36]CC1>C([O-])([O-])OCC.CN(C)C=O>[OH:17][C:16]1[CH:38]=[C:37]2[C:20]([C:16](=[O:17])[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:25][O:36]2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 540149872,4-Dihydroxy-phenyl-benzyl-ketone2×

Product 1

HCID 53768917-Hydroxyisoflavone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 53630039EthylorthoformateSolvent

Procedure

reacting 2,4-dihydroxy-phenyl-benzyl-ketone of formula (II) ##STR7## with ethyl orthoformate in dimethylformamide as solvent and in the presence of a catalyst consisting of morpholine, to yield 7-hydroxyisoflavone of formula (III) ##STR8## b) separating of product (III) from the reaction residue, c) alkylating of product (III) from step b) with isopropyl halide to obtain ipriflavone, wherein:

Sources & evidence

ORD record
ord-3696b9fb723f42a2a86d4864333d4635
Source dataset
uspto-grants-1999_10
Patent number
US05973169

Reaction notes

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