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

HRID 14461ノート

反応式

HRID 14461 の反応式
[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

参加物

5

反応物 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 68704522HCID 68704522、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-53cb518bd0a54f4e82fd9274a2a555d0
出典データセット
uspto-grants-2010_06
特許番号
US07732435B2

反応ノート

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