Dimethyl Sulfate → 1-(4,5-Dimethoxy-2-methoxycarbonylphenyl)-3,4-dihydroisoquinoline

HRID 65689Notes

Reaction equation

HRID 65689 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.O[C:9]12[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[C:19](=[O:30])[N:10]1[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=12>CO>[CH3:29][O:28][C:22]1[C:23]([O:26][CH3:27])=[CH:24][C:25]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]=2)=[C:20]([C:19]([O:6][CH3:7])=[O:30])[CH:21]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 2275755212b-Hydroxy-10,11-dimethoxy-5,6,8,12b-tetrahydro-isoindolo[1,2-a]isoquinol-8-one

Product 1

HCID 227575571-(4,5-Dimethoxy-2-methoxycarbonylphenyl)-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl sulphate (48 cc) is added to a suspension of 12b-hydroxy-10,11-dimethoxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinol-8-one (80.65 g) in methanol (563 cc) and the reaction mixture is heated under reflux for 6 hours. After concentration to 100 cc and the successive addition of water (300 cc) and then of 10N sodium hydroxide (70 cc), the mixture is extracted three times with ethyl acetate (total 400 cc). The combined organic solutions are washed three times with distilled water (total 400 cc), dried over anhydrous sodium sulphate, treated with decolourising charcoal (1 g), filtered and evaporated. 1-(4,5-Dimethoxy-2-methoxycarbonylphenyl)-3,4-dihydroisoquinoline (67.8 g), melting at 133° C., is thus obtained.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 6 hours
  3. concentrationAfter concentration to 100 cc
  4. additionthe successive addition of water (300 cc)
  5. extractionof 10N sodium hydroxide (70 cc), the mixture is extracted three times with ethyl acetate (total 400 cc)
  6. washThe combined organic solutions are washed three times with distilled water (total 400 cc)
  7. dry with materialdried over anhydrous sodium sulphate
  8. additiontreated with decolourising charcoal (1 g)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-6f9b99b6e68b4a00819632ca9a5ba3aa
Source dataset
uspto-grants-1978_12
Patent number
US04128650

Reaction notes

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