Morpholine → 7-Hydroxyisoflavone

HRID 6277

Reaction equation

HRID 6277 reaction equation
OC1C=C(O)C=CC=1[CH:9]([C:16]([CH:18]([C:25]1[CH:30]=[CH:29]C(O)=CC=1O)C1C=CC=CC=1)=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1CC[O:36]CC1.[CH2:39]([O:41][CH:42]([O-])[O-])[CH3:40]>CN(C)C=O>[OH:36][C:29]1[CH:40]=[C:39]2[C:18]([C:16](=[O:17])[C:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:42][O:41]2)=[CH:25][CH:30]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 53630039EthylorthoformateHCID 540149872,4-Dihydroxy-phenyl-benzyl-ketone

Product 1

HCID 53768917-HydroxyisoflavoneYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 g (0.219 mole) of a mixture of 2,4-dihydroxy-phenyl-benzyl-ketone, 20 ml of dimethyl-formamide, 2.6 ml of morpholine and 39.06 g (0.26 mole) of ethyl-orthoformate is stirred for 7 hours at 80°-90° C. After 25 minutes crystallization can be observed. At the end of the reaction time the crystallized suspension is diluted with 120 ml of chloroform and it is crystallized at 0° C. for 2 hours. After filtration the product is covered twice with 45 ml of chloroform and dried. 47.9 g of 7-hydroxy-isoflavone are obtained.

Workup

  1. customAfter 25 minutes crystallization
  2. additionAt the end of the reaction time the crystallized suspension is diluted with 120 ml of chloroform and it
  3. customis crystallized at 0° C. for 2 hours
  4. filtrationAfter filtration the product
  5. customdried

Sources & evidence

ORD record
ord-a8539b47ced44f24996e5458c2287ac2
Source dataset
uspto-grants-1993_09
Patent number
US05247102

Linked notes

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