Iodine → 5,6,7-Trimethoxy-4'-nitroflavone

HRID 1095274Notes

Reaction equation

HRID 1095274 reaction equation
[OH:1][C:2]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[C:3]=1[C:4](=[O:16])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.II>CS(C)=O>[CH3:26][O:25][C:17]1[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=[C:2]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[O:1]2

Participants

4

Reactant 2

HCID 807IodineHCID 727670692'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalcone

Product 1

HCID 102477335,6,7-Trimethoxy-4'-nitroflavoneYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 7a (0.80 g, 2.2 mmol) and iodine (20 mg) in DMSO (5 ml) was refluxed for 1 h, and then carefully poured onto crushed ice. The precipitate was filtered and washed with 20% Na2SO3. Recrystallization of the precipitate from acetone afforded 8 (0.73 g, 93%). 1H NMR (400 MHz, CDCl3) δ 3.91 (s, 3H), 3.97 (s, 3H), 3.98 (s, 3H), 6.74 (s, 1H), 6.82 (s, 1H), 8.03 (d, J=8.8 Hz, 2H), 8.34 (d, J=8.8 Hz, 2H).

Workup

  1. temperaturewas refluxed for 1 h
  2. additioncarefully poured
  3. customonto crushed ice
  4. filtrationThe precipitate was filtered
  5. washwashed with 20% Na2SO3
  6. customRecrystallization of the precipitate from acetone

Sources & evidence

ORD record
ord-f9b30e73b6994d6dafc448f02432370c
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Reaction notes

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