Hydrogen Bromide → 6-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-one

HRID 892203ノート

反応式

HRID 892203 の反応式
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:15])([CH3:14])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:15])([CH3:14])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 260Hydrogen BromideHCID 219318586-Methoxy-1,3,3-trimethylindolin-2-one

生成物 1

HCID 219317776-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-one

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
110 °C

実験手順

To a solution of 6-methoxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (601 mg, 2.93 mmol, example 79) in acetic acid (880 μL) is added hydrobromic acid (48% in H2O) (8.8 mL). The resulting solution is heated to reflux (105°110° C.), stirred 2 hrs, then cooled to room temp and concentrated under reduced pressure. The residue is dissolved in EtOAc and the organic layer washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by triturating with a small volume of ether to give the title compound as an off white solid. MS (ESI) 192 (M+H)+.

後処理

  1. temperatureThe resulting solution is heated
  2. temperaturecooled to room temp
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue is dissolved in EtOAc
  5. washthe organic layer washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified
  9. customby triturating with a small volume of ether

出典と根拠

ORDレコード
ord-cacefbc016e54dc696193dda239e8cb0
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

読み込み中…