Tetrahydrofuran → HCID 19976049, compound

HRID 1450274Notes

Reaction equation

HRID 1450274 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].[H-].[Na+].BrCC(OC)=[O:20].C(OCC)(=O)C.[O:29]1C[CH2:32][CH2:31][CH2:30]1>O>[CH3:32][C:31]([CH2:30][O:29][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:20]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 131528427-Nitro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 19976049HCID 19976049, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution consisting of 7-nitro-1,2,3,4-tetrahydroisoquinolin-1-one (2.0 g, 10.4 mmol) in tetrahydrofuran (300 mL) was added sodium hydride (500 mg, 60% suspension in oil, 12.5 mmol). To the resulting mixture was added methyl bromoacetate (1.1 mL, 11 mmol). After 3 hours, ethyl acetate (20 mL) was added followed by water (25 mL). The solution was concentrated and the resulting oil was partitioned between ethyl acetate and water (1:1,200 mL). The layers were separated and the organic layer was washed successively with water (1×100 mL) and brine (1 ×100 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was treated with ethyl acetate and a solid formed. The solution was filtered to give the title compound (1.6 g, 55% yield).

Workup

  1. concentrationThe solution was concentrated
  2. customthe resulting oil was partitioned between ethyl acetate and water (1:1,200 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed successively with water (1×100 mL) and brine (1 ×100 mL)
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionThe residue was treated with ethyl acetate
  9. customa solid formed
  10. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-7b05c25cad804bdc8a880cb00c89a609
Source dataset
uspto-grants-1997_02
Patent number
US05602145

Reaction notes

Loading…