Methanol → HCID 19976048, compound

HRID 1450276Notes

Reaction equation

HRID 1450276 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:15](OC)(=O)[CH:16]=C.[CH3:21][O-:22].[Na+].[CH3:24][OH:25]>>[CH2:15]([C:21]([CH2:24][O:25][N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:11]1=[O:14])=[O:22])[CH3:16]

Participants

5

Reactant 4

HCID 887MethanolHCID 7294Methyl AcrylateHCID 10942334Sodium MethoxideHCID 131528427-Nitro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 19976048HCID 19976048, compoundYield 69%

Procedure

To a solution consisting of 7-nitro-1,2,3,4-tetrahydroisoquinolin-1-one (3.0 g, 15.6 mmol), methyl acrylate (15 mL, 156 mmol) and methanol (50 m L) was added sodium methoxide (840 mg, 15.6 mmol). The resulting solution was refluxed overnight. The reaction solution was concentrated and the resulting residue was introduced unto a silica gel column equilibrated with ethyl acetate/Hexane (3:7). Elution was done with the same solvent system. Desired fractions were concentrated to give title compound (2.6 g, 69% yield).

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. concentrationThe reaction solution was concentrated
  3. additionthe resulting residue was introduced unto a silica gel column
  4. washElution
  5. concentrationDesired fractions were concentrated

Sources & evidence

ORD record
ord-91590c3c52fd4fc79a67103d5fcb4c2a
Source dataset
uspto-grants-1997_02
Patent number
US05602145

Reaction notes

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