Ethanolamine → 3-(4-Chlorophenyl)-8-fluoro-7-(2-hydroxyethylamino)-2-isopropyl-chromen-4-one

HRID 14461Notes

Reaction equation

HRID 14461 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([F:20])[C:13](F)=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:21]([CH3:23])[CH3:22])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:31]([CH2:33][NH2:34])[OH:32]>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([F:20])[C:13]([NH:34][CH2:33][CH2:31][OH:32])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:21]([CH3:22])[CH3:23])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 68704522HCID 68704522, compound

Product 1

HCID 687043963-(4-Chlorophenyl)-8-fluoro-7-(2-hydroxyethylamino)-2-isopropyl-chromen-4-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A stirred solution of 3-(4-chlorophenyl)-7,8-difluoro-2-isopropyl-chromen-4-one (3.94 g, 11.8 mmol), triethylamine (2.4 g, 3.2 ml, 23.6 mmol, 2 eq.) and ethanolamine (0.72 g, 0.71 ml, 11.8 mmol, 1 eq.) in N,N-dimethylacetamide (200 ml) is heated at 150° C. overnight. The reaction mixture is allowed to cool to room temperature and the solvent is removed by evaporation in vacuo. The residue is dissolved in ethyl acetate and washed with 2M HCl solution. The organic layer is washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford a brown oil. The oil is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:6) to afford the title compound.

Workup

  1. customthe solvent is removed by evaporation in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with 2M HCl solution
  4. washThe organic layer is washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customto afford a brown oil
  9. customThe oil is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:6)

Sources & evidence

ORD record
ord-53cb518bd0a54f4e82fd9274a2a555d0
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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