Ethanol → HCID 89464205, compound

HRID 2275396Notes

Reaction equation

HRID 2275396 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[C:9]([OH:12])[CH:10]=2)[CH2:5][CH2:4][N:3]=1.C([CH:17](Br)[C:18](=O)[C:19]([O-:21])=[O:20])C.[CH3:24][CH2:25]O>>[OH:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4][N:3]3[CH:17]=[C:18]([C:19]([O:21][CH2:24][CH3:25])=[O:20])[CH:1]=[C:2]32)=[CH:7][C:8]=1[O:13][CH3:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 6056986-methoxy-1-methyl-3,4-dihydroisoquinolin-7-olHCID 21948992Ethylbromopyruvate

Product 1

HCID 89464205HCID 89464205, compound

Procedure

To a solution of 1-methyl-7-hydroxy-6-methoxy-3,4-dihydroisoquinoline (100 mg) in EtOH (5 ml) was added dropwise under a nitrogen atmosphere ethylbromopyruvate (0.065 ml) and the reaction mixture was heated under reflux for 2 hours. The reaction mixture was allowed to cool to ambient temperature, quenched with a saturated aqueous NaHCO3 solution and extracted with ethyl acetate. 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 heated
  2. temperatureunder reflux for 2 hours
  3. customquenched with a saturated aqueous NaHCO3 solution
  4. extractionextracted with ethyl acetate
  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-008f0e764baf40209709184e4e89512e
Source dataset
uspto-grants-2015_09
Patent number
US09127007B2

Reaction notes

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