Potassium Iodide → 7-Iodo-3,4-dihydroisoquinolin-1(2H)-one
Reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][NH:12][C:13]2=[O:16])=[CH:8][CH:7]=1.[I-:17].[K+].C(OC(=O)C)C>Cl.O.CCCCCC.C(Cl)Cl.[Cu](I)I>[I:17][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][NH:12][C:13]2=[O:16])=[CH:8][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 0 °C
Procedure
NaNO2 (340 mg, 4.9382 mmol) was added to a solution of 7-amino-3,4-dihydro-2H-isoquinolin-1-one (I-32a: 800 mg, 4.9382 mmol) in concentrated HCl (2 mL) and water (2 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes. The resulting diazonium salt solution was added portion wise to a vigorously stirred biphasic mixture of DCM (25 mL), potassium iodide (4.9 g, 29.6242 mmol), copper iodide (47 mg, 0.25 mmol) and water (8 mL). The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was diluted with DCM. The organic layer was washed with 10% Na2S2SO3 solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (50% ethylacetate in hexane) afforded 640 mg of the product (44.50% yield).
Workup
- stirringThe resulting mixture was stirred at room temperature overnight
- washThe organic layer was washed with 10% Na2S2SO3 solution
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customPurification by column chromatography on silica gel (50% ethylacetate in hexane)
Sources & evidence
- ORD record
- ord-f9979c4512e048348d5cd4f06df08328
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946260B2
Reaction notes
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