2,3-Dihydrobenzo[g]quinolin-4(1H)-one → HCID 178516364, compound

HRID 650532Notes

Reaction equation

HRID 650532 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=2)[C:4](=[O:15])[CH2:3][CH2:2]1>O1CCCC1.[O-2].[Mn+4].[O-2]>[N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=2)[C:4]([OH:15])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 6075412,3-Dihydrobenzo[g]quinolin-4(1H)-one

Product 1

HCID 178516364HCID 178516364, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

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.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customThe crude reaction mixture
  4. filtrationwas filtered through a celite plug

Sources & evidence

ORD record
ord-5de97caa97aa4100a8cd176651a2683e
Source dataset
uspto-grants-2001_08
Patent number
US06274596B1

Reaction notes

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