Dimethylamine → HCID 11536679, compound

HRID 418838Notes

Reaction equation

HRID 418838 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[CH:10][C:9]2=[O:23]>C1COCC1>[CH3:1][N:2]([CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[CH:10][C:9]2=[O:23])[CH3:3]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 66650401HCID 66650401, compound

Product 1

HCID 11536679HCID 11536679, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (1 M solution in THF, 1.2 mL) was added to 6-bromomethyl-2-(4-hydroxyphenyl)chromen-4-one (206 mg, 0.62 mmol) dissolved in dry THF (10 mL). The reaction mixture was stirred at rt for 17 hr. Most of the solvent was then removed in vacuo and the yellowish residue was suspended in 20 mL of water. The resulting suspension was stirred at rt for 30 min and the solid was removed by filtration, washed with water, ether, and air-dried to afford 6-((dimethylamino)methyl)-2-(4-hydroxyphenyl)-4H-chromen-4-one (125 mg, 68%). MS (ES) m/z: 296.98 (M+1), 295.97 (M); Mp. 99-102° C.

Workup

  1. customMost of the solvent was then removed in vacuo
  2. stirringThe resulting suspension was stirred at rt for 30 min
  3. customthe solid was removed by filtration
  4. washwashed with water, ether
  5. customair-dried

Sources & evidence

ORD record
ord-661999be791443349f4ce05fb74f5ab5
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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