Iodine → HCID 22479029, compound

HRID 2086901Notes

Reaction equation

HRID 2086901 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][NH:8][CH2:7][C:6]2([CH3:16])[CH3:15].II.C([O-])(=O)C.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][CH2:7][C:6]2([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 517045Sodium AcetateHCID 12264703HCID 12264703, compound

Product 1

HCID 22479029HCID 22479029, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.0 g of 1,2,3,4-tetrahydro-6,7-dimethoxy-4,4-dimethyl-isoquinoline in 100 ml of ethanol is treated with 2.3 g of iodine and 0.49 g of sodium acetate and heated under reflux for 1 hour. The reaction mixture is cooled down and 30 ml of a 10% sodium thiosulphate-solution is added. The mixture is then diluted with water and extracted with dichloromethane (2×100 ml). The combined organic extracts are washed with brine, dried over sodium sulfate and concentrated in vacuo. The foamy residue is purified by chromatography (SiO2, dichloromethane-1% ammonia in methanol, 0-12%) to give the title compound as a yellowish oil (0.72 g), MS (ISP) 220.4 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction mixture is cooled down
  4. extractionextracted with dichloromethane (2×100 ml)
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe foamy residue is purified by chromatography (SiO2, dichloromethane-1% ammonia in methanol, 0-12%)

Sources & evidence

ORD record
ord-3093c2860cd74b738026a8ff00bcefc5
Source dataset
uspto-grants-2004_04
Patent number
US06727261B2

Reaction notes

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