Benzaldehyde → 8-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline
Reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1>C(OC(=O)C)(=O)C>[CH:1](=[C:17]1[C:18]2[N:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14][CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
In a nitrogen atmosphere, 150 mL of benzaldehyde was added to acetic anhydride (180 mL) solution of 65 mL of 5,6,7,8-tetrahydroquinoline, and stirred at 170° C. for 12 hours. The reaction liquid was cooled to room temperature, and the excess reagent was evaporated off under reduced pressure. Then, aqueous saturated sodium hydroxide solution was added thereto, and extracted with ethyl acetate; and the ethyl acetate layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was crystallized from ethyl acetate/hexane to obtain 96.4 g of the entitled compound as a pale brown solid.
Workup
- customThe reaction liquid
- temperaturewas cooled to room temperature
- customthe excess reagent was evaporated off under reduced pressure
- additionThen, aqueous saturated sodium hydroxide solution was added
- extractionextracted with ethyl acetate
- washand the ethyl acetate layer was washed with saturated saline water
- dry with materialdried with anhydrous sodium sulfate
- customThe solvent was evaporated off under reduced pressure
- customthe residue was crystallized from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-e6d33dd407d54de7a60a20ca474c8dc3
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855294B2
Reaction notes
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