2-Benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline → 6,7-Dichloro-1-(3,4,5-trimethyoxybenzyl)isoquinoline hydrochloride

HRID 247400Notes

Reaction equation

HRID 247400 reaction equation
C([N:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([Cl:20])=[C:14]([Cl:19])[CH:15]=2)[C:10]1([CH2:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=1)C#N)(=O)C1C=CC=CC=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[ClH:19].[Cl:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[Cl:20])[C:10]([CH2:23][C:24]1[CH:25]=[C:26]([O:34][CH3:35])[C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)=[N:9][CH:18]=[CH:17]2

Participants

4

Reactant 1

HCID 136795072-Benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline

Product 1

HCID 212949006,7-Dichloro-1-(3,4,5-trimethyoxybenzyl)isoquinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Benzyltriethylammonium chloride (0.118 g, 0.517 mmole) was added to a solution of 2.3 g (4.5 mmole) of 2-benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1, 2-dihydroisoquinoline in 40 ml of toluene. The stirred solution was flushed with nitrogen and then 19 ml of 50% sodium hydroxide solution was added in one portion. The reaction mixture was stirred and refluxed under nitrogen for 1.5 hours; it was then cooled and 25 ml of water and 25 ml of ethyl acetate were added. The organic layer was separated, washed (water, brine), dried (magnesium sulfate) and concentrated. The residue in a small volume of methanol was acidified with hydrogen chloride and ether was added to give 6,7-dichloro-1-(3,4,5-trimethyoxybenzyl)isoquinoline hydrochloride as white crystals, melting at 211°-212° C., after recrystallization from methanol-ether.

Workup

  1. customThe stirred solution was flushed with nitrogen
  2. addition19 ml of 50% sodium hydroxide solution was added in one portion
  3. temperaturerefluxed under nitrogen for 1.5 hours
  4. temperatureit was then cooled
  5. addition25 ml of water and 25 ml of ethyl acetate were added
  6. customThe organic layer was separated
  7. washwashed (water, brine)
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated
  10. additionwas added

Sources & evidence

ORD record
ord-8de9cfe62198426d936381af7e3b4d2b
Source dataset
uspto-grants-1987_11
Patent number
US04707485

Reaction notes

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