Sodium Carbonate → 3-chloro-7,8-dihydroisoquinolin-5(6H)-one

HRID 1175119Notes

Reaction equation

HRID 1175119 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=NO)[C:10]=2[CH:11]=1.C([O-])([O-])=[O:15].[Na+].[Na+]>CC(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:15])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 136342879HCID 136342879, compound

Product 1

HCID 595583933-chloro-7,8-dihydroisoquinolin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

3-Chloro-7,8-dihydro-6H-isoquinolin-5-one oxime (9.10 g; 46.3 mmol) dissolved in acetone (105 ml) and HClconc (105 ml) is heated at 60° C. for 1 hour. The reaction mixture is poured on 2N Na2CO3 and extracted with ethyl acetate three times, the organic phases are combined, dried over Na2SO4 and evaporated to dryness. Chromatography (SiO2; Hexanes/acetone 85:15) yields the desired ketone as yellowish crystals. 1H-NMR (400 MHz; DMSO-d6): 8.57 (s, 1H); 7.66 (s, 1H); 2.96 (m, 2H); 2.71 (m, 2H); 2.10 (m, 2H). MS (m/z) ES+: 182 (MH+).

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-4982e881548e4283ba00fa5ee2663898
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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