Hydrochloric Acid → (S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyridazin-3(2H)-one

HRID 1527973ノート

反応式

HRID 1527973 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[N:14][C:13]=2[O:18]C)=[O:11])=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[C:13](=[O:18])[NH:14][N:15]=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 86684800(S)-3-(4-Bromophenyl)-1-(3-methoxypyridazin-4-yl)-3-o-tolylpropan-1-one

生成物 1

HCID 86684801(S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyridazin-3(2H)-one収率 108.4%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

To a solution of (S)-3-(4-bromophenyl)-1-(3-methoxypyridazin-4-yl)-3-o-tolylpropan-1-one (example 4, step 1; 312 mg, 759 μmol) in 1,4-dioxane (9 ml) was added 37% aq. hydrochloric acid solution (1.27 ml, 15.2 mmol) and the resulting solution was first stirred at 60° C. for 3 h and then for 2½ h at 80° C. After cooling the reaction mixture was poured onto ice water and ethyl acetate, neutralized with sat. aq. sodium hydrogen carbonate solution and the pH was adjusted to 6.85 with 1 M aq. potassium phosphate buffer solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound (327 mg, quantitative), which was directly used in the next step. Light red foam, MS: 397.1 [M+H]+.

後処理

  1. waitfor 2½ h at 80° C
  2. temperatureAfter cooling the reaction mixture
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-e88cb08bba59434da709ff9c82be9d36
出典データセット
uspto-grants-2015_07
特許番号
US09090565B2

反応ノート

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