1,2,3,4-Tetrahydroisoquinoline → 2-(3-Nitropyridin-4-yl)-1,2,3,4-tetrahydroisoquinoline

HRID 1988828Notes

Reaction equation

HRID 1988828 reaction equation
[H-].[Na+].[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][NH:4]1.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21]>CN(C)C=O.O.C(OCC)(=O)C>[N+:20]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[N:4]1[CH2:5][CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:3]1)([O-:22])=[O:21]

Participants

7

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 24758Sodium hydrideHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 687057032-(3-Nitropyridin-4-yl)-1,2,3,4-tetrahydroisoquinolineYield 89.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60%, 386.4 mg, 9.66 mmol) was added at 0° C. to a solution of 1,2,3,4-tetrahydroisoquinoline (1.06 ml, 8.05 mmol) in N,N-dimethylformamide (30 ml) and stirred for 10 minutes at the same temperature. 4-Chloro-3-nitropyridine (1.124 g, 7.09 mmol) prepared in Step 1 was added to the reaction mixture, which was stirred for 2 hours at room temperature, diluted with a mixture of water (10 ml) and ethyl acetate (100 ml), and then washed with water (100 ml) twice. The separated organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled compound as a yellow solid (1.13 g, 89.3%).

Workup

  1. stirringwas stirred for 2 hours at room temperature
  2. washwashed with water (100 ml) twice
  3. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73dec7413f3345879ab68929a08d88b9
Source dataset
uspto-grants-2010_01
Patent number
US07642269B2

Reaction notes

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