Allyl bromide → 2-(Prop-2-en-1-yl)-1,2,3,4-tetrahydrobenzo[g]isoquinolin-5-amine

HRID 1679665Notes

Reaction equation

HRID 1679665 reaction equation
[NH2:1][C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH2:7]2.[CH2:16](Br)[CH:17]=[CH2:18].C(N(CC)CC)C.[OH-].[Na+]>C(Cl)(Cl)Cl.O>[CH2:18]([N:6]1[CH2:5][CH2:4][C:3]2[C:8](=[CH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:2]=2[NH2:1])[CH2:7]1)[CH:17]=[CH2:16]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 203617021,2,3,4-Tetrahydrobenzo[g]isoquinolin-5-amine

Product 1

HCID 203617132-(Prop-2-en-1-yl)-1,2,3,4-tetrahydrobenzo[g]isoquinolin-5-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 7.9 g of 5-amino-1,2,3,4-tetrahydrobenzo[g]isoquinoline, 5.3 g of allyl bromide, 2.6 g of triethylamine in 50 ml of anhydrous chloroform is heated to the boil for 4.5 hours while stirring. 100 ml of water are added to the resulting solution after cooling to room temperature, the solution is made alkaline with 40% caustic soda solution, and the organic phase is separated off. The organic solution is washed neutral with water, dried over sodium sulphate and concentrated by evaporation. The residue is recrystallized twice from methanol. M.Pt. of the title compound: 74° - 76°.

Workup

  1. temperatureis heated to the boil for 4.5 hours
  2. customthe organic phase is separated off
  3. washThe organic solution is washed neutral with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue is recrystallized twice from methanol
  7. custom74° - 76°

Sources & evidence

ORD record
ord-63187a476e0a4fe59ff306a70cdb27be
Source dataset
uspto-grants-1978_03
Patent number
US04081543

Reaction notes

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