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

HRID 988257ノート

反応式

HRID 988257 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収率 88.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

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) 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 495 mg of title compound as an off white solid. MS (ESI) 192 (M+H)+.

後処理

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux (105°-110° C.)
  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-6a35bd728ef049bf88003f43df7d2006
出典データセット
uspto-grants-2003_10
特許番号
US06635655B1

反応ノート

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