Hydrochloric Acid → 7-Methoxy-3-(4-methoxyphenyl)quinoline

HRID 1035596Notes

Reaction equation

HRID 1035596 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:12]=O)[CH:10]=O)=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:19]([CH:12]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH:10]=[N:22]2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 108243-MethoxyanilineHCID 38493702-(4-Methoxyphenyl)malondialdehyde

Product 1

HCID 594434847-Methoxy-3-(4-methoxyphenyl)quinolineYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-methoxyphenyl)malondialdehyde (797 mg, 4.48 mmol, 1 eq) in 20 ml of ethanol are added m-anisidine (551 mg, 4.48 mmol, 1 eq) and 10 ml of conc. HCl. The reaction mixture is stirred at 80° C. for 3 days, and after cooling to RT, the reaction is stopped by adding a 10% sodium carbonate solution. The mixture is extracted with dichloromethane, and the organic phase is dried over MgSO4, filtered, and the solvent is removed in vacuum on a rotary evaporator. After purification by column chromatography with hexane/ethyl acetate as the eluent, the product was obtained in a yield of 19% (221 mg).

Workup

  1. temperatureafter cooling to RT
  2. extractionThe mixture is extracted with dichloromethane
  3. dry with materialthe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuum on a rotary evaporator
  6. customAfter purification by column chromatography with hexane/ethyl acetate as the eluent
  7. customthe product was obtained in a yield of 19% (221 mg)

Sources & evidence

ORD record
ord-47d494823b044ef9900ba5211ff99525
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

Loading…