Water → 7-[3-[4-(Carbomethoxymethoxy)phenethylamino]-2-hydroxypropoxy]flavone Maleate

HRID 478082Notes

Reaction equation

HRID 478082 reaction equation
[OH:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][CH2:7][NH:8][CH2:9][CH:10]([OH:30])[CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:29])[CH:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:20]3)=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38].[OH2:41]>CN(C=O)C>[C:19]([OH:41])(=[O:20])/[CH:23]=[CH:36]\[C:37]([OH:39])=[O:38].[C:37]([CH2:36][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][CH2:9][CH:10]([OH:30])[CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:29])[CH:18]=[C:19]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[O:20]3)=[CH:15][CH:14]=2)=[CH:31][CH:32]=1)([O:39][CH3:40])=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 14626316HCID 14626316, compound

Product 1

HCID 146263197-[3-[4-(Carbomethoxymethoxy)phenethylamino]-2-hydroxypropoxy]flavone MaleateYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

7-[3-[(4-Hydroxyphenethyl)amino]-2-hydroxypropoxy]flavone (10.8 g, 25.1 mmol), Example 13, was dissolved in 20 ml of warm DMF at 50°-60° C. and then cooled to -20° C. Sodium hydride (1.2 g, 0.0251 mmol) was added portionwise to the above cooled solution, stirred at -20° C. for 1 hour, and then cooled to -40° C. Methyl bromoacetate (3.8 g, 25.1 mmol) was added dropwise to the stirred solution and the reaction mixture was kept at this temperature for 2 hours and at RT overnight. The reaction was poured into 1.5 l of water, the water decanted, and the residue washed with two portions of water. The gummy material was then purified by flash column chromatography, eluting with CHCl3 --MeOH (20:1). The isolated material (2.7 g) was recrystallized from methanol, and the crystallized solid was treated with 30 ml of ethanol and maleic acid (0.3 g) to give the title compound as white crystals, mp 154°-156° C., 1.5 g (10% yield).

Workup

  1. temperaturecooled to -40° C
  2. waitthe reaction mixture was kept at this temperature for 2 hours and at RT overnight
  3. customthe water decanted
  4. washthe residue washed with two portions of water
  5. customThe gummy material was then purified by flash column chromatography
  6. washeluting with CHCl3 --MeOH (20:1)
  7. customThe isolated material (2.7 g) was recrystallized from methanol
  8. additionthe crystallized solid was treated with 30 ml of ethanol and maleic acid (0.3 g)

Sources & evidence

ORD record
ord-dc6241a72ce440c2b3f8362577e595a0
Source dataset
uspto-grants-1989_12
Patent number
US04889941

Reaction notes

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