Toluene → Quinoline, 1,2-dihydro-1-acetyl-
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(OCC)C.O>[C:27]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1)(=[O:29])[CH3:28]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Quinoline (19.37 g, 150 mmol) was dissolved in anhydrous diethyl ether (500 ml) and cooled to 0° C. under inert atmosphere. DIBAL, 1.5 M in toluene (100 ml, 150 mmol) was added dropwise over 2 hrs and the reaction mixture was stirred at 0° C. for 30 min. Acetic anhydride (500 ml) was added dropwise over 30 min and the reaction mixture was stirred at 0° C. for 30 min. H2O was added cautiously. The reaction mixture was extracted with diethyl ether and concentrated to give N-acetyl-1,2-dihydroquinoline (11.5 g, 44%).
Workup
- stirringthe reaction mixture was stirred at 0° C. for 30 min
- extractionThe reaction mixture was extracted with diethyl ether
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5373c13aa88d408fa314936f77500c39
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517992B2
Reaction notes
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