Iodine → 6-iodo-4'-methylaminoflavone

HRID 215669Notes

Reaction equation

HRID 215669 reaction equation
[I:1]I.C([Sn](CCCC)(CCCC)[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH3:25])=[CH:20][CH:19]=1)=[CH:12][C:11]2=[O:26])CCC.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[I:1][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH3:25])=[CH:20][CH:19]=1)=[CH:12][C:11]2=[O:26]

Participants

5

Reactant 3

HCID 807IodineHCID 11613563HCID 11613563, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 116322426-iodo-4'-methylaminoflavone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A chloroform solution of iodine (1.5 ml, 1 M) was added to a chloroform solution (20 ml) that contained compound 8 (100 mg, 0.185 mmol) at room temperature. The obtained mixture was reacted at room temperature for 10 minutes, and a saturated sodium bisulfite aqueous solution (15 ml) was then added thereto, so as to terminate the reaction. The chloroform layer was separated, and it was then dried over sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure, and the residue was then subjected to silica gel column chromatography using ethyl acetate/hexane (1/2) as an elution solvent, so as to obtain a product of interest, 6-iodo-4′-methylaminoflavone (compound 10). Yield: 20 mg (yield constant: 28.7%) 1H NMR (300 MHz, CDCl3) δ8.53 (s, 1H), 7.90 (d, J=9.0 Hz, 1H), 7.75 (d, J=8.4 Hz, 2H), 7.28 (d, J=10.8 Hz, 1H), 6.64-6.69 (m, 3H), 4.15 (s, 1H), 2.93 (s, 3H). MS m/z 377 (M+).

Workup

  1. customat room temperature
  2. customThe obtained mixture was reacted at room temperature for 10 minutes
  3. customso as to terminate
  4. customthe reaction
  5. customThe chloroform layer was separated
  6. dry with materialit was then dried over sodium sulfate
  7. distillationThereafter, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-7b4ea587df7d4e989b4921161f990e8e
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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