5,6,7-Trimethoxy-4'-nitroflavone → 4'-Amino-5,6,7-trimethoxyflavone

HRID 1095276Notes

Reaction equation

HRID 1095276 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:26])[CH:6]=[C:7]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=1)[O:8]2>O1CCOCC1.[Pd]>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([C:7]2[O:8][C:9]3[C:4]([C:5](=[O:26])[CH:6]=2)=[C:3]([O:2][CH3:1])[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=3)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 102477335,6,7-Trimethoxy-4'-nitroflavone

Product 1

HCID 100193254'-Amino-5,6,7-trimethoxyflavoneYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of the flavone 8 (0.07 g, 0.2 mmol) in dioxane (10 ml) was hydrogenated at 40 psi in the presence of 5% palladium on charcoal (20 mg) for 8 h and the catalyst was filtered off. Dioxane was removed from the filtrate under reduced pressure to give 10a (0.05 g, 87%). 1H NMR (400 MHz, CDCl3) δ 3.98 (s, 3H), 3.94 (s, 3M), 3.95 (s, 3H), 6.45 (s, 1H), 6.71 (d, J=8.8 Hz, 2H), 6.75 (s, 1H), 7.65 (d, J=8.8 Hz, 2H).

Workup

  1. filtrationthe catalyst was filtered off
  2. customDioxane was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c49fcb27aa4e4cab88b949bae0f227e3
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Reaction notes

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