Sodium Hydroxide → 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 1014301Notes

Reaction equation

HRID 1014301 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12](=[O:14])[O-])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[C:12](=[O:14])[NH:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86644179HCID 86644179, compound

Product 1

HCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-oneYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of {2-[3-(methyloxy)phenyl]ethyl}carbamate (30 g crude) and polyphosphoric acid (116 g) was maintained at 120-140° C. for 1 hr. After cooling to room temperature, water was added. The solution was adjusted to pH=9 with 6N sodium hydroxide and the organic products extracted with ethyl acetate. The combined organic layers were concentrated under reduced pressure and the residue was purified by column chromatography to afford 6-(methyloxy)-3,4-dihydro-1(2H)-isoquinolinone (10 g, 40%). 1H NMR(CDCl3) δ 8.0 (1H), 6.85 (1H), 6.7 (1H), 6.35 (1H), 3.85 (3H), 3.55 (2H), 2.95 (2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe organic products extracted with ethyl acetate
  3. concentrationThe combined organic layers were concentrated under reduced pressure
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9bce92d167e347d8b6b896a875963bfe
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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