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

HRID 35735

Reaction equation

HRID 35735 reaction equation
[C:1]([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)[CH:10]1[C:21]#[N:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[CH2:28]Cl.[OH-].[Na+].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]([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([CH2:28][C:27]1[CH:30]=[C:31]([O:35][CH3:36])[C:32]([O:33][CH3:34])=[C:25]([O:24][CH3:23])[CH:26]=1)[C:21]#[N:22])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 136795062-Benzoyl-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline

Product 1

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

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.7 g (5.17 mmole) of 2-benzoyl-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline, 1.16 g (5.37 mmole) of 3,4,5-trimethoxybenzyl chloride and 0.118 g (0.517 mmole) of benzyltriethylammonium chloride in 25 ml of toluene, under nitrogen, was added 7.2 ml of 50% sodium hydroxide solution. The mixture was stirred vigorously at ambient temperature for 2 hours, and then 25 ml of water and 25 ml of methylene chloride was added. The organic layer was separated, washed with water, dried over magnesium sulphate and concentrated to give 2-benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline, m.p. 193°-195° C., after recrystallization from acetonitrile.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e8a16f824bc74929abe7fc502c9cf233
Source dataset
uspto-grants-1988_08
Patent number
US04767862

Linked notes

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