Ethanol → HCID 13380437, compound

HRID 2275398Notes

Reaction equation

HRID 2275398 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.C(=O)([O-])[O-].[K+].[K+].C([CH:24](Br)[C:25](=O)[C:26]([O-:28])=[O:27])C.C([O-])(O)=O.[Na+].[CH2:36](O)[CH3:37]>>[CH3:15][O:14][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[O:12][CH3:13])[C:2]1=[CH:1][C:25]([C:26]([O:28][CH2:36][CH3:37])=[O:27])=[CH:24][N:3]1[CH2:4][CH2:5]2

Participants

6

Reactant 5

HCID 702EthanolHCID 11430Potassium CarbonateHCID 226523,4-Dihydro-6,7-dimethoxy-1-methylisoquinolineHCID 516892Sodium BicarbonateHCID 21948992Ethylbromopyruvate

Product 1

HCID 13380437HCID 13380437, compound

Procedure

To a mixture of 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline (2 g) and potassium carbonate (2.4 g) in ethanol (50 ml) was added dropwise ethylbromopyruvate (1.22 ml). The reaction mixture was refluxed for 3 hrs. The reaction was allowed to cool to ambient temperature before a saturated aqueous NaHCO3 solution was added. The aqueous phase was extracted with ethyl acetate twice. The combined organic layers were washed with brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with heptane and increasing amounts of ethyl acetate.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hrs
  2. additionwas added
  3. extractionThe aqueous phase was extracted with ethyl acetate twice
  4. washThe combined organic layers were washed with brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel eluting with heptane
  9. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-b100e88525e84c878382939633c5444c
Source dataset
uspto-grants-2015_09
Patent number
US09127007B2

Reaction notes

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