Benzene → HCID 58492563, compound

HRID 68141Notes

Reaction equation

HRID 68141 reaction equation
C1C=CC=CC=1.[CH2:7]([O:10][C:11]1[C:12]([NH2:21])=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH3:9].[C:22]([CH:25]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:26](OCC)=[O:27])(=O)[CH3:23].C(OCC)(=O)C>CCCCCC>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([C:25]2[C:26](=[O:27])[C:13]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[CH:20]=[C:11]([O:10][CH2:7][CH2:8][CH3:9])[C:12]=3[NH:21][C:22]=2[CH3:23])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 8857Ethyl AcetateHCID 12577863Ethyl 2-(4-methoxyphenyl)-3-oxobutanoateHCID 212799043-Propoxynaphthalen-2-ylamine

Product 1

HCID 58492563HCID 58492563, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a benzene solution (38 ml) containing 3-propoxynaphthalen-2-ylamine (600 mg, 2.98 mmol) and ethyl α-acetyl-4-methoxyphenylacetate (1.41 g, 5.96 mmol) was added 85 mg of Amberlyst 15 (Sigma-Aldrich). The resulting mixture was heated under reflux for 20 hours using a Dean-Stark trap. The reaction mixture was cooled to room temperature, filtered to remove resin, and then the filtrate was concentrated under reduced pressure. Diphenyl ether (2.8 ml) was added to the residue, and the mixture was then heated with a mantle heater and stirred for 70 minutes under reflux. The resulting reaction mixture was cooled to room temperature, and then directly purified using silica gel column chromatography (dichloromethane:methanol=80:1→70:1). The purified product was concentrated under reduced pressure, giving an oily substance (800 mg, yield: 72%). Ethyl acetate and n-hexane were added to the thus-obtained oily substance to crystallize and then recrystallized from ethyl acetate, giving a pale yellow powder of 2-(4-methoxyphenyl)-3-methyl-5-propoxy-4H-benzo[f]quinolin-1-one (290 mg).

Workup

  1. additionwas added 85 mg of Amberlyst 15 (Sigma-Aldrich)
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 20 hours
  4. filtrationfiltered
  5. customto remove resin
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionDiphenyl ether (2.8 ml) was added to the residue
  8. temperaturethe mixture was then heated with a mantle heater
  9. temperatureunder reflux
  10. customThe resulting reaction mixture
  11. temperaturewas cooled to room temperature
  12. customdirectly purified
  13. concentrationThe purified product was concentrated under reduced pressure
  14. customgiving an oily substance (800 mg, yield: 72%)
  15. customto crystallize
  16. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bd794614aa9f415481ca693716300b61
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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