Ethyl chloroacetate → HCID 15908311, compound

HRID 1274979Notes

Reaction equation

HRID 1274979 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2.[H-].[Na+].Cl[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 15908311HCID 15908311, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-methoxy-1,2,3,4-tetrahydro-1-oxo-isoquinoline, Sall and Grunewald, J. Med. Chem. 1987, 30, 2208-2216 (0.39 mmol) and NaH (0.17 g, 0.43 mmol, 60% oil dispersion) in THF (5 mL) is heated to reflux for 1 h and then allowed to cool to RT. Ethyl chloroacetate (0.43 mmol) is added and the mixture is allowed to stir for 1 h. The mixture is quenched with H2O (10 mL) and washed with EtOAc. The organic layers are combined, washed with H2O (10 mL) and concentrated to an oil which is purified by (silica gel, gradient, 10-33% CH3OH/CH2Cl2) to afford the title compound.

Workup

  1. temperatureto reflux for 1 h
  2. customThe mixture is quenched with H2O (10 mL)
  3. washwashed with EtOAc
  4. washwashed with H2O (10 mL)
  5. concentrationconcentrated to an oil which
  6. customis purified by (silica gel, gradient, 10-33% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-f2c8798c0b1e48a3861105e5412dd77e
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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