6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → HCID 19974622, compound

HRID 1451650Notes

Reaction equation

HRID 1451650 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][NH:8][CH2:7][CH2:6]2.[Br:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:18]>C(O)C.C(Cl)Cl>[BrH:15].[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([C:17](=[O:18])[CH2:16][N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)=[CH:24][CH:23]=1)([O-:27])=[O:26]

Participants

5

Reactant 2

HCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 668402-Bromo-4'-nitroacetophenone

Product 1

HCID 19974622HCID 19974622, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (15.63 g) and 2-bromo-4'-nitroacetophenone (16.47 g) in a mixture of ethanol (150 ml) and methylene chloride (150 ml) was heated at 60° for 24 hours. After cooling to room temperature yellow crystals appeared. These were collected by filtration and dried in vacuo to give the title compound (9.4 g); MP: 216°. NMR(D6 -DMSO) includes signals at d 3.6(6H,s,2×OCH3); 4.2(2H,s,N--CH2 --Ph); 4.95(2H,s,CO--CH2 --N); 6.6(2H,aromatics isoquinoline); 8(4H,m,aromatics).

Workup

  1. temperaturewas heated at 60° for 24 hours
  2. filtrationThese were collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-406fec2ab4d94b85a803d4b6060120d7
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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