Ammonia → HCID 49864197, compound

HRID 250783Notes

Reaction equation

HRID 250783 reaction equation
C1(=O)OC(=O)CC1.C(O)(=O)CCC(N)=O.C([NH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][C:25]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[C:24]([OH:36])[C:23]2=[O:37])(=O)C.Cl.N>C(O)C>[NH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][C:25]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[C:24]([OH:36])[C:23]2=[O:37]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 12522Succinamic acidHCID 49864161N-(3-hydroxy-4-oxo-2-phenyl-chromen-6-yl)acetamide

Product 1

HCID 49864197HCID 49864197, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With substantial amounts of 4 in hand, the next steps were to form the 6-acetamidoflavonol. Thus, the acetophenone 4 was treated with benzaldehyde and base to effect a Claisen-Schmidt condensation affording the chalcone 5 in 71% yield. The chalcone 5 was treated with alkaline hydrogen peroxide to enable an Algar-Flynn-Oyamada reaction, giving 6-acetamidoflavonol 6 in 50% yield. The next step was to unveil the 6-amino group of 6 to allow coupling with succinic anhydride for installation of the succinamic acid side chain. The 6-acetamidoflavonol 6 was treated with 5 M HCl in ethanol at reflux, followed by neutralization with aqueous ammonia to give 6-aminoflavonol.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-09f8c105d7134ada80c098906d1d2c90
Source dataset
uspto-grants-2011_01
Patent number
US07863323B1

Reaction notes

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