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

HRID 1843880Notes

Reaction equation

HRID 1843880 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.C(OC(=O)C)C>CCCCCC>[C:4]1(=[O:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][NH:5]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 247630Ethyl phenethylcarbamate

Product 1

HCID 1508963,4-dihydroisoquinolin-1(2H)-oneYield 9.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

Phenethyl-carbamic acid ethyl ester (I-23a: 9 g, 46.875 mmol) and poly phosphoric acid (187.5 g) were taken in a flask and the flask was heated to 120° C. for 4 hours. The reaction was monitored by TLC (30% ethylacetate in hexane). The reaction mixture was partitioned between chilled water and ethylacetate. The resulting mixture was stirred at 115° C. for 2 hours to afford the crude product. Purification by column chromatography on silica gel (60% ethylacetate in hexane) afforded 0.090 g of the product (9.1% yield).

Workup

  1. customThe reaction mixture was partitioned
  2. temperaturebetween chilled water and ethylacetate
  3. customto afford the crude product
  4. customPurification by column chromatography on silica gel (60% ethylacetate in hexane)

Sources & evidence

ORD record
ord-dc7745c020d54c2ba4ba7e4330201587
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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