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

HRID 2117210노트

반응식

HRID 2117210 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 219317776-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-one수율 88.3%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-31a78c4131cf4c28ba08ecffbec30e70
출처 데이터셋
uspto-grants-2008_10
특허 번호
USRE040558E1

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