2,3-dihydro-1H-benzo[g]quinolin-4-one

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

Procedure: To 500 mg of 2,3-Dihydrobenzo[g]quinolin-4(IH)-one (1, 2.53 mmol) in 25 mL of dry tetrahydrofuran (0.25 M) under a nitrogen atmosphere was added 1.76 g manganese(IV) oxide (8 equivalents). The reaction mixture was heated to reflux and monitored by TLC until completion. The crude reaction mixture was filtered through a celite plug using 5% methanol in methylene chloride to afford 445 mg of relatively clean benzo[g]quinolin-4-ol (6) in 90% yield. Subsequently, the phenol was directly subjected to the halogenation conditions without further purification. The reaction mixture was heated to reflux The crude reaction mixture was filtered through a celite plug

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

Procedure: To 1 g of 2,3-Dihydrobenzo[g]quinolin-4(1H)-one (5) (5.07 mmol) in 20 mL of toluene (0.25 M) under a nitrogen atmosphere was added 1.5 g of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ, 1.3 equivalents). The reaction mixture was heated to reflux and monitored by TLC until completion (approximately 2 h). After cooling to rt, the mixture was concentrated in vacuo then filtered through a silica plug using 10% methanol in methylene chloride to afford crude phenol (6). Subsequently, the crude phenol was directly subjected to the halogenation conditions of step 2. The reaction mixture was heated to reflux monitored by TLC until completion (approximately 2 h) the mixture was concentrated in vacuo then filtered through a silica plug

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

Procedure: To 500 mg of 2,3-Dihydrobenzo[g]quinolin-4(IH)-one (1, 2.53 mmol) in 25 mL of dry tetrahydrofuran (0.25 M) under a nitrogen atmosphere was added 1.76 g manganese(IV) oxide (8 equivalents). The reaction mixture was heated to reflux and monitored by TLC until completion. The crude reaction mixture was filtered through a celite plug using 5% methanol in methylene chloride to afford 445 mg of relatively clean benzo[g]quinolin-4-ol (6) in 90% yield. Subsequently, the phenol was directly subjected to the halogenation conditions without further purification. The reaction mixture was heated to reflux The crude reaction mixture was filtered through a celite plug

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

Procedure: To 1 g of 2,3-Dihydrobenzo[g]quinolin-4(1H)-one (5) (5.07 mmol) in 20 mL of toluene (0.25 M) under a nitrogen atmosphere was added 1.5 g of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ, 1.3 equivalents). The reaction mixture was heated to reflux and monitored by TLC until completion (approximately 2 h). After cooling to rt, the mixture was concentrated in vacuo then filtered through a silica plug using 10% methanol in methylene chloride to afford crude phenol (6). Subsequently, the crude phenol was directly subjected to the halogenation conditions of step 2. The reaction mixture was heated to reflux monitored by TLC until completion (approximately 2 h) the mixture was concentrated in vacuo then filtered through a silica plug