1,2,3,4-Tetrahydroisoquinoline → 3,4-Dihydroisoquinoline

HRID 2293127Notes

Reaction equation

HRID 2293127 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.BrN1C(=O)CCC1=O.[OH-].[Na+]>ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide

Product 1

HCID 767053,4-Dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18.8 ml of 1,2,3,4-tetrahydroisoquinoline(0.15M) was dissolved in 400 ml of dichloromethane; and 29.4 g of N-bromosuccinimide(0.165M) was slowly added thereto at room temperature followed by stirring for 30 minutes. To this, 100 ml of aqueous sodium hydroxide(30%) was added and further stirred for an hour. The organic layer was separated, washed with water and extracted from aqueous hydrochloric acid solution. Ammonia water was added to adjust the pH to 9; and extracted from dichloromethane, washed with water, dried over anhydrous sodium sulfate and concentrated to give 18.5 g of the title compound in oil form.

Workup

  1. customat room temperature
  2. stirringfurther stirred for an hour
  3. customThe organic layer was separated
  4. washwashed with water
  5. extractionextracted from aqueous hydrochloric acid solution
  6. additionAmmonia water was added
  7. extractionand extracted from dichloromethane
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-35490ee65a8f43bf9b6bccd883275ecf
Source dataset
uspto-grants-1997_11
Patent number
US05686458

Reaction notes

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