4-Phenyl-3,4-dihydro-1H-benzo[h]quinolin-2-one → HCID 66818900, compound

HRID 2092358Notes

Reaction equation

HRID 2092358 reaction equation
[C:1]1([CH:7]2[C:16]3[C:11](=[C:12]4[CH:20]=[CH:19][CH:18]=[CH:17][C:13]4=[CH:14][CH:15]=3)[NH:10][C:9](=[O:21])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S]>C(O)(=O)C>[C:1]1([C:7]2[C:16]3[C:11](=[C:12]4[CH:20]=[CH:19][CH:18]=[CH:17][C:13]4=[CH:14][CH:15]=3)[NH:10][C:9](=[O:21])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 28297134-Phenyl-3,4-dihydro-1H-benzo[h]quinolin-2-oneHCID 5362487Sulfur2×

Product 1

HCID 66818900HCID 66818900, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
205 °C

Procedure

A mixture of 4-Phenyl-3,4-dihydro-1H-benzo[h]quinolin-2-one (0.55 g, 2.0 mmol) and sulfur (0.06 g, 2 mmol) was stirred at 205° C. for 0.5 hr under a nitrogen atmosphere. A second batch of sulfur (0.06 g, 2 mmol) was added and the solution stirred for 12 hr at 205° C. The product was dissolved in hot acetic acid and filtered. The clear filtrate upon cooling deposited crystals that were separated by filtration and washed with acetic acid and water followed by vacuum drying to afford the title compound (0.08 g, 0.30 mmol).

Workup

  1. stirringthe solution stirred for 12 hr at 205° C
  2. filtrationfiltered
  3. temperatureThe clear filtrate upon cooling
  4. customwere separated by filtration
  5. washwashed with acetic acid and water
  6. customdrying

Sources & evidence

ORD record
ord-35728be90a21446bb156cd7de36402ed
Source dataset
uspto-grants-2013_05
Patent number
US08440705B2

Reaction notes

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