1,2-Dimethoxyethane → 5-(4-Chlorophenyl)-N-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 736438Notes

Reaction equation

HRID 736438 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:15])[CH2:7]2.[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>O>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]3[C:3]=2[CH2:4][CH2:5][N:6]([CH3:15])[CH2:7]3)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 100160105-Bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 234358215-(4-Chlorophenyl)-N-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5-bromo-N-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline (4.07 g, 15 mmol), 4-chlorophenylboronic acid (3.5 g, 22.5 mmol), sodium carbonate (8.0 g, 75.5 mmol), 1,2-dimethoxyethane (60 ml), water (30 ml) and tetrakis(triphenyl-phosphine)palladium(0) (0.20 g, 0.17 mmol) was stirred at reflux for 3.5 h. Water (50 ml) was added and the mixture was extracted with ethyl acetate (100 ml). The crude mixture was recrystallized from ethanol (96%). Yield 3.62 g (80%). Mp 162-163° C.

Workup

  1. temperatureat reflux for 3.5 h
  2. extractionthe mixture was extracted with ethyl acetate (100 ml)
  3. customThe crude mixture was recrystallized from ethanol (96%)

Sources & evidence

ORD record
ord-3b181741bc2a4b5588d658cebb7ad6ab
Source dataset
uspto-grants-2009_09
Patent number
US07595336B2

Reaction notes

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