Carbamic acid, N-[2-(3-methoxyphenyl)ethyl]-, ethyl ester → 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 1696523Notes

Reaction equation

HRID 1696523 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][CH2:7][NH:8][C:9](=O)[O:10]CC>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:9](=[O:10])[NH:8][CH2:7][CH2:6]2

Participants

3

Reactant 1

HCID 10822969Carbamic acid, N-[2-(3-methoxyphenyl)ethyl]-, ethyl ester

Product 1

HCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-oneYield 138%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-methoxyphenethylcarbamate (7.32 g, 32.8 mmol) and polyphosphoric acid (30 g) was heated at 120° C. for 2 h after which H2O (100 mL) was added and the mixture was cooled to RT. The mixture was extracted with EtOAc (6×100 mL), dried (MgSO4) and concentrated to yield crude 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one (8.0 g, 138%) as a sticky gum. 1H NMR (400 MHz, acetone-d6): δ 7.88 (d, J=8.4 Hz. 1H), 7.04 (brS, 1H), 6.87 (dd, J=8.4, and 2.4 Hz, 1H), 6.82 (d, J=2.4 Hz, 1H), 3.84 (s, 3H), 3.49 (t, J=6.4 Hz, 2H), 2.94 (t, J=6.2 Hz, 2H); MS (ESI) m/z: 178.0 (M+H+).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc (6×100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-221cf3bdf9b0447d9c8fc95465be5a9a
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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