1,2,3,4-Tetrahydroisoquinoline → HCID 11483278, compound

HRID 2305548Notes

Reaction equation

HRID 2305548 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](O)=[CH:3][C:2]=1O.[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1.O=P(Cl)(Cl)[Cl:25].[OH-].[Na+]>CO.C(Cl)Cl>[Cl:25][C:2]1[CH:3]=[C:4]([N:14]2[CH2:15][CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

7

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1785165532-hydroxy-1H-quinolin-4-one

Product 1

HCID 11483278HCID 11483278, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2,4-quinolinediol (1 g, 6.2 mmol) and 1,2,3,4-tetrahydroisoquinoline (1.57 ml, 12.4 mmol) was heated overnight under argon at 200° C. Reaction mixture was cooled to room temperature, diluted with MeOH, stirred for 30 min. and filtered. The solid obtained was refluxed overnight in the presence of POCl3 (3 ml). The reaction mixture was cooled to room temperature and poured into a 0° C. stirring mixture of 5N NaOH (50 ml) and CH2Cl2 (50 ml). After 15 min., aqueous phase was extracted with CH2Cl2 (2×), combined organic phases were washed with H2O, dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate, 97:3 then 9:1) to provide 2-chloro-4-(3,4-dihydro-1H-isoquinolin-2-yl)-quinoline (0.1 g, 5%) as a colorless oil, MS: m/e=295.3 (M+H+).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. filtrationfiltered
  4. customThe solid obtained
  5. temperatureThe reaction mixture was cooled to room temperature
  6. additionpoured into a 0° C.
  7. stirringstirring
  8. waitAfter 15 min.
  9. extractionaqueous phase was extracted with CH2Cl2 (2×)
  10. washwere washed with H2O
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated
  13. customThe residue was chromatographed over silica gel (hexane-ethyl acetate, 97:3

Sources & evidence

ORD record
ord-834541378dad41ba9164433e4a9bce34
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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