Dimethylformamide → 1-(4-Butylbenzyl)isoquinoline

HRID 597765Notes

Reaction equation

HRID 597765 reaction equation
CN(C)C=O.[H-].[Na+].[C:8]([CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]1C(=O)C1C=CC=CC=1)#N.[CH2:28]([C:32]1[CH:39]=[CH:38][C:35](CCl)=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31]>O>[CH2:28]([C:32]1[CH:39]=[CH:38][C:35]([CH2:8][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][N:11]=2)=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 182273Benzene, 1-butyl-4-(chloromethyl)-HCID 2304882-Benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile

Product 1

HCID 99002251-(4-Butylbenzyl)isoquinolineYield 17.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide (1.8 ml) solution of 60% sodium hydride (16 mg, 0.40 mmol), a dimethylformamide (3.6 ml) solution of 1-cyano-2-benzoyl-1,2-dihydroisoquinoline (100 mg, 0.38 mmol) synthesized according to the literature of Org. Synth., VI, 115 (1988), and 4-n-butylbenzylchloride (70 mg, 0.38 mmol) was added dropwise under nitrogen atmosphere at −16° C., and was further stirred at room temperature for 30 minutes. Water was added, this was concentrated, and toluene and water were added to this residue. The toluene layer was washed with water, dried over potassium carbonate, and concentrated. To an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added, and this was refluxed for 2 hours. After concentration, toluene and water were added. The toluene layer was washed with water, then dried over calcium carbonate, and then concentrated. The residue was purified by silica gel column chromatography to give 18 mg of the aforementioned compound of the formula (Ia).

Workup

  1. concentrationthis was concentrated
  2. additiontoluene and water were added to this residue
  3. washThe toluene layer was washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated
  6. additionTo an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added
  7. temperaturethis was refluxed for 2 hours
  8. concentrationAfter concentration, toluene and water
  9. additionwere added
  10. washThe toluene layer was washed with water
  11. dry with materialdried over calcium carbonate
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-63e429487d474d50b8f9c5f09af3289a
Source dataset
uspto-grants-2011_03
Patent number
US07897387B2

Reaction notes

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