Ethyl Acetate → 7-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 1843911Notes

Reaction equation

HRID 1843911 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)C.C(OC(=O)C)C>CCCCCC>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][NH:5][C:4]2=[O:3])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 887923HCID 887923, compound

Product 1

HCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-oneYield 22.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
145 °C

Procedure

[2-(4-methoxy-phenyl)-ethyl]-carbamic acid ethyl ester (I-35a: 10 g, 44.84 mmol) was added to PPA (100 mg) at 145° C. The resulting mixture was stirred at 145° C. for 45 minutes. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was quenched with chilled water and extracted with ethylacetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (40% ethylacetate in hexane) afforded 1.8 g of the product (22.69% yield).

Workup

  1. customThe reaction mixture was quenched with chilled water
  2. extractionextracted with ethylacetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (40% ethylacetate in hexane)

Sources & evidence

ORD record
ord-4a7e072529584ba48356b51228f30284
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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