6-iodo-3,4-dihydro-1H-quinolin-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Iodo-3,4-dihydroquinolin-2(1H)-one (1.50 g; 5.50 mmol), sodium cyanide (0.54 g; 11.0 mmol), copper (I) iodide (0.105 g; 0.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.32 g; 0.3 mmol) were combined in a flask equipped with a reflux condenser. The flask was subjected to several evacuation-nitrogen purge cycles followed by the addition of acetonitrile (25 mL). The reaction was heated to reflux for 5 hours. After cooling, the reaction was diluted with ethyl acetate (200 mL), filtered through CELITE diatomaceous earth and rinsed with copious amounts of ethyl acetate. The organic solution was washed twice with brine (50 mL), dried over sodium sulfate, filtered through a fritted funnel, and the volatiles were removed under vacuum. The crude residue was crystallized from methanol, which afforded the title compound. equipped with a reflux condenser purge cycles followed by the addition of acetonitrile (25 mL) The reaction was heated to reflux for 5 hours After cooling the reaction was diluted with ethyl acetate (200 mL) filtered through CELITE diatomaceous earth rinsed with copious amounts of ethyl acetate The organic solution was washed twice with brine (50 mL) dried over sodium sulfate filtered through a fritted funnel the volatiles were removed under vacuum The crude residue was crystallized from methanol, which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,4-Dihydroquinolin-2(1H)-one (7.5 g; 51 mmol) and silver (I) sulfate (17.5 g; 56.1 mmol) were suspended in ethanol (250 mL). A solution of iodine in ethanol (250 mL) was added slowly to the reaction over 1 hour. After 6 hours, the reaction was filtered through CELITE diatomaceous earth and washed copiously with methanol. The volatiles were removed under vacuum and the crude residue was triturated with ether. The solids were collected on a fritted funnel and dried under vacuum. This provided the title compound. the reaction was filtered through CELITE diatomaceous earth washed copiously with methanol The volatiles were removed under vacuum the crude residue was triturated with ether The solids were collected on a fritted funnel dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Iodo-3,4-dihydroquinolin-2(1H)-one (1.50 g; 5.50 mmol), sodium cyanide (0.54 g; 11.0 mmol), copper (I) iodide (0.105 g; 0.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.32 g; 0.3 mmol) were combined in a flask equipped with a reflux condenser. The flask was subjected to several evacuation-nitrogen purge cycles followed by the addition of acetonitrile (25 mL). The reaction was heated to reflux for 5 hours. After cooling, the reaction was diluted with ethyl acetate (200 mL), filtered through CELITE diatomaceous earth and rinsed with copious amounts of ethyl acetate. The organic solution was washed twice with brine (50 mL), dried over sodium sulfate, filtered through a fritted funnel, and the volatiles were removed under vacuum. The crude residue was crystallized from methanol, which afforded the title compound. equipped with a reflux condenser purge cycles followed by the addition of acetonitrile (25 mL) The reaction was heated to reflux for 5 hours After cooling the reaction was diluted with ethyl acetate (200 mL) filtered through CELITE diatomaceous earth rinsed with copious amounts of ethyl acetate The organic solution was washed twice with brine (50 mL) dried over sodium sulfate filtered through a fritted funnel the volatiles were removed under vacuum The crude residue was crystallized from methanol, which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,4-Dihydroquinolin-2(1H)-one (7.5 g; 51 mmol) and silver (I) sulfate (17.5 g; 56.1 mmol) were suspended in ethanol (250 mL). A solution of iodine in ethanol (250 mL) was added slowly to the reaction over 1 hour. After 6 hours, the reaction was filtered through CELITE diatomaceous earth and washed copiously with methanol. The volatiles were removed under vacuum and the crude residue was triturated with ether. The solids were collected on a fritted funnel and dried under vacuum. This provided the title compound. the reaction was filtered through CELITE diatomaceous earth washed copiously with methanol The volatiles were removed under vacuum the crude residue was triturated with ether The solids were collected on a fritted funnel dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Iodo-3,4-dihydroquinolin-2(1H)-one (1.50 g; 5.50 mmol), sodium cyanide (0.54 g; 11.0 mmol), copper (I) iodide (0.105 g; 0.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.32 g; 0.3 mmol) were combined in a flask equipped with a reflux condenser. The flask was subjected to several evacuation-nitrogen purge cycles followed by the addition of acetonitrile (25 mL). The reaction was heated to reflux for 5 hours. After cooling, the reaction was diluted with ethyl acetate (200 mL), filtered through CELITE diatomaceous earth and rinsed with copious amounts of ethyl acetate. The organic solution was washed twice with brine (50 mL), dried over sodium sulfate, filtered through a fritted funnel, and the volatiles were removed under vacuum. The crude residue was crystallized from methanol, which afforded the title compound. equipped with a reflux condenser purge cycles followed by the addition of acetonitrile (25 mL) The reaction was heated to reflux for 5 hours After cooling the reaction was diluted with ethyl acetate (200 mL) filtered through CELITE diatomaceous earth rinsed with copious amounts of ethyl acetate The organic solution was washed twice with brine (50 mL) dried over sodium sulfate filtered through a fritted funnel the volatiles were removed under vacuum The crude residue was crystallized from methanol, which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,4-Dihydroquinolin-2(1H)-one (7.5 g; 51 mmol) and silver (I) sulfate (17.5 g; 56.1 mmol) were suspended in ethanol (250 mL). A solution of iodine in ethanol (250 mL) was added slowly to the reaction over 1 hour. After 6 hours, the reaction was filtered through CELITE diatomaceous earth and washed copiously with methanol. The volatiles were removed under vacuum and the crude residue was triturated with ether. The solids were collected on a fritted funnel and dried under vacuum. This provided the title compound. the reaction was filtered through CELITE diatomaceous earth washed copiously with methanol The volatiles were removed under vacuum the crude residue was triturated with ether The solids were collected on a fritted funnel dried under vacuum