3,4-Dihydro-6,7-dimethoxy-1-methylisoquinoline → HCID 54178010, compound

HRID 1738890Notes

Reaction equation

HRID 1738890 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH2:4][N:3]=1.Cl[CH2:17][C:18](=O)[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])O.[Na+]>C(O)C>[CH3:23][O:22][C:20](=[O:21])[CH2:19][C:18]1[CH:1]=[C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[CH2:5][CH2:4][N:3]2[CH:17]=1

Participants

5

Reactant 3

HCID 226523,4-Dihydro-6,7-dimethoxy-1-methylisoquinolineHCID 36240Methyl 4-chloroacetoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 54178010HCID 54178010, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.3 g (50.0 mmol) of 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline, 8.3 g (55.0 mmol) of methyl 4-chloroacetoacetate and 12.6 g (150 mmol) of sodium hydrogen carbonate in 100 ml of ethanol are heated at reflux for 5 hours. After evaporation to dryness, the residue is taken up in 250 ml of dichloromethane and washed twice with 100 ml of water each time. After drying the organic phase over magnesium sulphate and then concentrating, the residue (15.5 g) is chromatographed on 500 g of silica (eluant: dichloromethane) to yield 8.5 g of the expected product (theory: 15.1 g).

Workup

  1. temperatureat reflux for 5 hours
  2. customAfter evaporation to dryness
  3. washwashed twice with 100 ml of water each time
  4. dry with materialAfter drying the organic phase over magnesium sulphate
  5. concentrationconcentrating
  6. customthe residue (15.5 g) is chromatographed on 500 g of silica (eluant: dichloromethane)

Sources & evidence

ORD record
ord-3cf19cb39748452da4c561bf1d6eee45
Source dataset
uspto-grants-1999_10
Patent number
US05965575

Reaction notes

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