1,2,3,4-Tetrahydroisoquinoline → HCID 18433086, compound

HRID 2305547Notes

Reaction equation

HRID 2305547 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([N:14]2[CH2:15][CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[CH:11]=1

Participants

5

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 6075032,4-Dichloroquinoline

Product 1

HCID 18433086HCID 18433086, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,4-dichloroquinoline (0.2 g, 1 mmol) and 1,2,3,4-tetrahydroisoquinoline (0.282 ml, 2.2 mmol) in toluene (2 ml) was refluxed during 18 hours then cooled to room temperature. The reaction mixture was diluted with CH2Cl2 and quenched with a saturated solution of NaHCO3. Aqueous phase was extracted with CH2Cl2 (2×). Combined organic phases were washed with H2O, dried over NaSO4, and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate, 97:3) to provide 4-chloro-2-(3,4-dihydro-1H-isoquinolin-2-yl)-quinoline (0.235 g, 79%) as a yellow oil, MS: m/e=295.3 (M+H+).

Workup

  1. customquenched with a saturated solution of NaHCO3
  2. extractionAqueous phase was extracted with CH2Cl2 (2×)
  3. washCombined organic phases were washed with H2O
  4. dry with materialdried over NaSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel (hexane-ethyl acetate, 97:3)

Sources & evidence

ORD record
ord-b10049dae1ac46a9a69923297418cbcb
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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