2-Methyl-6,7,8-trimethoxy-1[4,5,6-triethoxy-7-nitro-3-phthalidyl]-1,2,3,4-tetrahydro-isoquinoline → 458L

HRID 1155505Notes

Reaction equation

HRID 1155505 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:16][CH3:17])[C:6]([O:14][CH3:15])=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]1[CH:18]1[C:27]2[C:22](=[C:23]([N+:37]([O-])=O)[C:24]([O:34][CH2:35][CH3:36])=[C:25]([O:31][CH2:32][CH3:33])[C:26]=2[O:28][CH2:29][CH3:30])[C:20](=[O:21])[O:19]1.[H][H]>[Ni].C(O)C>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:16][CH3:17])[C:6]([O:14][CH3:15])=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]1[CH:18]1[C:27]2[C:22](=[C:23]([NH2:37])[C:24]([O:34][CH2:35][CH3:36])=[C:25]([O:31][CH2:32][CH3:33])[C:26]=2[O:28][CH2:29][CH3:30])[C:20](=[O:21])[O:19]1

Participants

5

Reactant 2

HCID 128009352-Methyl-6,7,8-trimethoxy-1[4,5,6-triethoxy-7-nitro-3-phthalidyl]-1,2,3,4-tetrahydro-isoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 166433458LYield 76.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

270 g of the nitro derivative (a) is added to 1.570 liters of ethanol and 21 g of Raney nickel in an autoclave. Hydrogen is added under a pressure of 10 atmospheres and the reactants are heated at a temperature of 65° while stirring. After 1 hour 45 minutes the theoretical volume of hydrogen has been absorbed. The solution is cooled and filtered. The ethanol is distilled in vacuo, the residue is dissolved in 0.6 l of methanol, 60 g of potassium hydroxide tablets are added, and the mixture is heated under reflux for 1 hour while stirring. The mixture is cooled and allowed to crystallise. 194.5 g (yield=76%) of 2-methyl-6,7,8-trimethoxy-1-(4,5,6-triethoxy-7-amino-3-phthalidyl)-1,2,3,4-tetrahydro-isoquinoline is obtained in the form of white crystals having a melting point of 144° and exhibiting only a single spot when analysed by thin layer chromatography.

Workup

  1. temperaturethe reactants are heated at a temperature of 65°
  2. customAfter 1 hour 45 minutes the theoretical volume of hydrogen has been absorbed
  3. temperatureThe solution is cooled
  4. filtrationfiltered
  5. distillationThe ethanol is distilled in vacuo
  6. dissolutionthe residue is dissolved in 0.6 l of methanol
  7. addition60 g of potassium hydroxide tablets are added
  8. temperaturethe mixture is heated
  9. temperatureunder reflux for 1 hour
  10. stirringwhile stirring
  11. temperatureThe mixture is cooled
  12. customto crystallise

Sources & evidence

ORD record
ord-a081d94380cb400795c870c6fbcf0a90
Source dataset
uspto-grants-1981_11
Patent number
US04302458

Reaction notes

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