Ethyl iodoacetate → (1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester

HRID 406482

Reaction equation

HRID 406482 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[H-].[Na+].I[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11])[CH3:20]

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 1508963,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 59764846(1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,4-dihydro-2H-isoquinolin-1-one (0.250 g, 1.70 mmol) in toluene (5 mL) was added sodium hydride (60% in mineral oil, 0.049 g, 2.04 mmol) and the resulting suspension was heated at about reflux for about 1 h. The reaction mixture was cooled at room temperature and ethyl 2-iodoacetate (0.364 g, 1.70 mmol) was added dropwise and the mixture was again heated at about reflux for about 12 h. The reaction mixture was cooled at room temperature and filtered, rinsed with toluene. The filtrate was concentrated in vacuo to provide (1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester as a peach oil (0.336 g, 1.44 mmol). The crude material was used in subsequent reactions without further purification.

Workup

  1. temperaturethe resulting suspension was heated at
  2. temperatureabout reflux for about 1 h
  3. temperaturethe mixture was again heated at
  4. temperatureabout reflux for about 12 h
  5. temperatureThe reaction mixture was cooled at room temperature
  6. filtrationfiltered
  7. washrinsed with toluene
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1d1de92b70de414f8fecb0ebfe936e74
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Linked notes

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