Sodium Carbonate → 5-Bromo-3-methyl-indol-2-one

HRID 990637

반응식

HRID 990637 반응식
[Br:1]Br.[CH3:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:13].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Br:1][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[C:4]([CH3:3])[C:5](=[O:13])[N:6]=2)[CH:11]=1

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 1509233-MethyloxindoleHCID 517045Sodium Acetate

생성물 1

HCID 220193765-Bromo-3-methyl-indol-2-one수율 93.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

Under an atmosphere of nitrogen, bromine (0.96 g, 6.0 mmol) in acetic acid (5 cm3). was added drop wise to a solution of 3-methyl-2-indolinone (0.8749 g, 6.0 mmol) (Kende, et al, Synth. Commun., 12, 1, 1982) and sodium acetate (0.50 g, 6.0 mmol) in acetic acid (10 cm3). The reaction was stirred at room temperature for 3.5 h. Saturated sodium carbonate was added to quench the reaction. The water layer was extracted EtOAc (×3), dried (MgSO4), filtered, and evaporated to give the title compound (1.26 g, 93%), Mp=119-120° C.; 1H NMR (DMSO) δ 1.32 (d, 3H, J=7.66 Hz), 3.45 (q, 1H, J=7.62 Hz), 6.77 (d, 1H, J=8.23 Hz), 7.46 (s, 1H), 7.36-7.33 (m, 1H), 10.4 (s, 1H); IR (KBr) 3200, 1725 cm−1; MS (EI) m/z 224/226 (M−H)−; CHN calculated for C9H8BrNO: C, 47.82; H, 3.57; N, 6.20; Found: C, 47.44; H, 3.42; N, 6.04.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionThe water layer was extracted EtOAc (×3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-502dabb16e32404ebd2739f1cd3b52a5
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06462032B1

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