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

HRID 222109ノート

反応式

HRID 222109 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6375Nitromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-37aaf707785e4c22b2607c5bdda78c50
出典データセット
uspto-grants-2012_06
特許番号
US08207180B2

反応ノート

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