2-Bromopropane → 2-(Propan-2-yl)-1,2,3,4-tetrahydrobenzo[g]isoquinolin-5-amine

HRID 1679664Notes

Reaction equation

HRID 1679664 reaction equation
[CH:1](Br)([CH3:3])[CH3:2].[NH2:5][C:6]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][CH2:11]2.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH2:5][C:6]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][N:10]([CH:1]([CH3:3])[CH3:2])[CH2:11]2

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 10340Sodium CarbonateHCID 203617021,2,3,4-Tetrahydrobenzo[g]isoquinolin-5-amine

Product 1

HCID 203617122-(Propan-2-yl)-1,2,3,4-tetrahydrobenzo[g]isoquinolin-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 5.2 g of isopropyl bromide in 10 ml of ethanol is added dropwise at room temperature to a mixture of 8.0 g of 5-amino-1,2,3,4-tetrahydrobenzo[g]isoquinoline [see Example 4]and 4.5 g of anhydrous sodium carbonate in 30 ml of ethanol. The reaction mixture is then boiled for 6 hours. The solvent is removed by evaporation, and the residue is treated with water. The resulting mixture is extracted with methylene chloride. The organic phase is washed with water, dried over potassium carbonate and evaporated. The title compound is obtained as a residue which is recrystallized from hexane/isopropanol (M.Pt. 112° - 113°).

Workup

  1. customThe solvent is removed by evaporation
  2. additionthe residue is treated with water
  3. extractionThe resulting mixture is extracted with methylene chloride
  4. washThe organic phase is washed with water
  5. dry with materialdried over potassium carbonate
  6. customevaporated

Sources & evidence

ORD record
ord-3d77a2795d514b44bdf500405138c57d
Source dataset
uspto-grants-1978_03
Patent number
US04081543

Reaction notes

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