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

HRID 222109Notes

Reaction equation

HRID 222109 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-37aaf707785e4c22b2607c5bdda78c50
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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