Methyl phenethylcarbamate → 3,4-dihydroisoquinolin-1(2H)-one

HRID 1450272Notes

Reaction equation

HRID 1450272 reaction equation
C[O:2][C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O>O>[C:3]1(=[O:2])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][NH:5]1

Participants

3

Reactant 1

HCID 4380476Methyl phenethylcarbamate

Product 1

HCID 1508963,4-dihydroisoquinolin-1(2H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of polyphosphoric acid (200 mL) at 140° C. N-methoxycarbonyl-phenethylamine (28 g, 0.16 mol) was added portionwise over a 5 hour period. The reaction solution was poured into cold water (400 mL) and extracted with methylene chloride (5×200 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give the title compound (17.96 g, 86% yield).

Workup

  1. customat 140° C
  2. extractionextracted with methylene chloride (5×200 mL)
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f335b70dc1834bccb896eb5f1aaf7adf
Source dataset
uspto-grants-1997_02
Patent number
US05602145

Reaction notes

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