Water → 2-Phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbaldehyde

HRID 222109노트

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HRID 222109 반응식
[C:1]1([C:7]2[NH:19][C:10]3=[C:11]4[C:16](=[CH:17][CH:18]=[C:9]3[CH:8]=2)[CH:15]=[N:14][CH:13]=[CH:12]4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH:25]([O:27]C)Cl.O>C(Cl)Cl.[N+](C)([O-])=O>[C:1]1([C:7]2[NH:19][C:10]3=[C:11]4[C:16](=[CH:17][CH:18]=[C:9]3[C:8]=2[CH:25]=[O:27])[CH:15]=[N:14][CH:13]=[CH:12]4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) ChlorideHCID 687096312-phenyl-1H-pyrrolo[2,3-f]isoquinoline

생성물 1

HCID 866402502-Phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbaldehyde수율 51%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6375Nitromethane용매

실험 절차

To a solution of 2-phenyl-1H-pyrrolo[2,3-f]isoquinoline XIXA (2.75 mmol) in DCM (13 mL) and nitromethane (13 mL), cooled to 0° C., aluminum chloride (8.25 mmol) and dichloromethylmethylether (5.5 mmol) were added dropwise. The mixture was kept at 4° C. overnight and poured dropwise into stirred ice-cooled water. The solid product was filtered and the layers were separated. The aqueous layer was extracted with DCM and AcOEt. The combined organic layers, washed with water, dried (Na2SO4) and concentrated, were joined to the previously described solid affording the title compound in 51% yield. ESI (+) MS: m/z 273 (MH+). 1H NMR: 7.66-7.71 (m, 3H), 7.91-7.96 (m, 2H), 8.19 (d, J=8.79, 1H), 8.71 (d, J=8.55, 1H), 8.79 (d, J=6.35, 1H), 8.93 (d, J=6.35, 1H), 9.77 (s, 1H), 10.12 (s, 1H), 13.80 (bs, 1H).

후처리

  1. additionpoured dropwise
  2. filtrationThe solid product was filtered
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with DCM and AcOEt
  5. washThe combined organic layers, washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-37aaf707785e4c22b2607c5bdda78c50
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207180B2

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