p-Toluenesulfonic acid → 2-phenyl-1H-pyrrolo[2,3-f]isoquinoline

HRID 222107Notes

Reaction equation

HRID 222107 reaction equation
C(=N[NH:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][N:20]=[CH:21]2)(C1C=CC=CC=1)C1C=CC=CC=1.[C:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=O)[CH3:27].CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[C:29]1([C:26]2[NH:15][C:16]3=[C:17]4[C:22](=[CH:23][CH:24]=[C:25]3[CH:27]=2)[CH:21]=[N:20][CH:19]=[CH:18]4)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7410AcetophenoneHCID 59226081N-benzhydrylidene-N'-isoquinolin-5-yl-hydrazine

Product 1

HCID 687096312-phenyl-1H-pyrrolo[2,3-f]isoquinolineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-benzhydrylidene-N′-isoquinolin-5-yl-hydrazine 4A (1.4 mmol) and acetophenone (2.1 mmol) in EtOH (7 mL), pTSA (5.6 mmol) was added and the mixture was submitted to microwaves at 120° C. for 1 h. The solvent was removed, the residue was dissolved in DCM and washed with aq saturated NaHCO3. The organic layer was dried (Na2SO4) and concentrated. The crude material was then purified by chromatography on silica gel (eluant: hexane/AcOEt 4:6) affording the title compound (58% yield). ESI (+) MS: m/z 245 (MH+). 1H NMR (500 MHz): 7.16 (d, J=2.20, 1H), 7.37 (t, J=7.45, 1H), 7.53 (t, J=7.81, 2H), 7.63 (d, J=8.79, 1H), 7.83 (d, J=8.79, 1H), 8.00 (d, J=7.32, 2H), 8.44 (d, J=5.62, 1H), 8.56 (d, J=5.62, 1H), 9.22 (bs, 1H), 12.40 (bs, 1H).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with aq saturated NaHCO3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude material was then purified by chromatography on silica gel (eluant: hexane/AcOEt 4:6)

Sources & evidence

ORD record
ord-8cfa32a3bf984cb283130379b8208493
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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