Methylamine → 2-(N-Methylamino)-7-hydroxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

HRID 529247Notes

Reaction equation

HRID 529247 reaction equation
Br[C:2]1[O:3][C:4]2[C:24]([O:25]C(=O)C)=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.[CH3:31][NH2:32]>C(#N)C>[CH3:31][NH:32][C:2]1[O:3][C:4]2[C:24]([OH:25])=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Product 1

HCID 248801162-(N-Methylamino)-7-hydroxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuranYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran (20 mg, 0.066 mmol) in acetonitrile (3 mL) was added the solution of methyamine (1 mL, excess as reactant and base), and the reaction mixture was stirred at room temperature for 1 hour when the precipitates appeared. The solvent was distilled under vacuo and the crude was dissolved in tetrahydrofuran (2 mL), 1M hydrochloric acid (1 mL) was added and the reaction mixture was stirred for 1 hour then diluted with dichloromethane (10 mL) and washed with water. The organic layer was dried over magnesium sulfate and solvent was distilled under vacuo. The crude was purified by PTLC (eluent=Hexane:ethylacetate:triethylamine; 2:8:1%) to gave the title compound as a yellow-green solid (5 mg, 29%); 1H NMR (300 MHz, CDCl3) δ 8.91 (broad, 1H, NH), 6.93 (s, 2H, benzoyl Hs), 6.59 (d, 1H, J=8.56 Hz), 6.46 (d, 1H, J=8.51 Hz), 5.61 (bs, 1H, OH), 3.91 (s, 3H, OMe), 3.86 (s, 3H, OMe), 3.84 (s, 6H, 2×OMe), 3.28 (d, 3H, J=5.28 Hz).

Workup

  1. distillationThe solvent was distilled under vacuo
  2. dissolutionthe crude was dissolved in tetrahydrofuran (2 mL)
  3. addition1M hydrochloric acid (1 mL) was added
  4. stirringthe reaction mixture was stirred for 1 hour
  5. additionthen diluted with dichloromethane (10 mL)
  6. washwashed with water
  7. dry with materialThe organic layer was dried over magnesium sulfate and solvent
  8. distillationwas distilled under vacuo
  9. customThe crude was purified by PTLC (eluent=Hexane:ethylacetate:triethylamine; 2:8:1%)

Sources & evidence

ORD record
ord-fdea546de5c844eb97594c7d231d6179
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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