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Sulfuric Acid → 2-Bromo-12H-chromeno[2,3-b]quinolin-12-one

HRID 717682
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반응식

HRID 717682 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:6]([CH:19]=O)[C:5]2=[O:21].OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]1=[N:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH:19]=[C:6]1[C:5]2=[O:21]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

3

반응물 2

HCID 1118Sulfuric AcidHCID 866606206-Bromo-4-oxo-2-(phenylamino)-4H-chromene-3-carbaldehyde

생성물 1

HCID 666150262-Bromo-12H-chromeno[2,3-b]quinolin-12-one수율 77%

실험 절차

To the product of Step A (1 g; 2.92 mmol) concentrated H2SO4 (1 ml) was gently added with stirring. The mixture was kept in sealed vial for 24 h, at room temperature, than poured onto ice water and extracted with CH2Cl2 (50 ml). The organic layer was washed with NaHCO3 solution, H2O, dried over MgSO4 and filtered. The filtrate was distilled off and the residue was crystallized from CH3CN to give the title compound (0.73 g, 77%), as green yellow solid. 1H-NMR (CDCl3) 9.28 (s, 1H); 8.44 (d, 1H, J=2.1 Hz); 8.1-8.06 (m, 2H); 7.94-7.84 (m, 2H); 7.63 (t, 1H, J=7.88 Hz); 7.51 (d, 1H, J=8.83 Hz).

후처리

  1. customsealed vial for 24 h
  2. addition
at room temperature, than poured onto ice water
  • extractionextracted with CH2Cl2 (50 ml)
  • washThe organic layer was washed with NaHCO3 solution, H2O
  • dry with materialdried over MgSO4
  • filtrationfiltered
  • distillationThe filtrate was distilled off
  • customthe residue was crystallized from CH3CN
  • 출처 및 근거

    ORD 기록
    ord-c1b6e19884c64fccad3d83b5d57bbfda
    출처 데이터셋
    uspto-grants-2015_11
    DOI
    10.6084/m9.figshare.5104873.v1
    특허 번호
    US09193716B2

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