Ammonia → 6-Chloro-3,4-dihydroisoquinolin-1(2H)-one

HRID 2277582Notes

Reaction equation

HRID 2277582 reaction equation
C[O:2][C:3](=O)[NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1.N>>[Cl:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[C:3](=[O:2])[NH:4][CH2:5][CH2:6]2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 897069HCID 897069, compound

Product 1

HCID 193756376-Chloro-3,4-dihydroisoquinolin-1(2H)-oneYield 39.1%

Conditions

Temperature
120 °C

Procedure

Under N2 protection, a mixture of [2-(3-chloro-phenyl)-ethyl]-carbamic acid methyl ester (5.0 g, 23.4 mmol) and PPA (polyphosphoric acid) (20 g) in a 250 mL round-bottom flask was vigorously stirred at 120° C. for 2 hours. After cooling to room temperature, the reaction mixture was treated with ice-water and aqueous ammonia solution to adjust the pH to 8. Then, the mixture was then extracted with EtOAc, and the organic layer was washed with brine, dried over anhy. Na2SO4 and filtered. After removal of solvent under reduced pressure, the crude product obtained was further washed with ethyl ether to give title compound (1.66 g, 39%) as a white solid. MS: 182.0 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThen, the mixture was then extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4 and filtered
  6. customAfter removal of solvent under reduced pressure
  7. customthe crude product obtained
  8. washwas further washed with ethyl ether

Sources & evidence

ORD record
ord-30778ba399ee41ed9caf598fbed29c9d
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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