O-Xylene → 1,5-Diazabicyclo(5,4,0)undec-5-ene
Reaction equation
O=[N:2][C:3](=O)[C:4](=O)[C:5]1[NH:6]C2C(=CC=1)C=CC1=NC=CC=21.C1(C)[C:21]([CH3:26])=[CH:22][CH:23]=[CH:24][CH:25]=1>C1(C)C=CC=CC=1>[N:2]12[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[CH:26]=[N:6][CH2:5][CH2:4][CH2:3]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The formula (XXXVI) 2-(2-imidazolin-2-yl)quinolinecarboxylate esters can also be prepared from a formula (XXXVIII) dioxopyrroloquinoline acetamide, wherein R1, R2, X, L, M, Q and R7 are as described above, by cyclization thereof with a strong base, such as 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU) in the presence of an inert organic solvent such as xylene or toluene to give the crude imidazopyrroloquinolinedione of formula (XXXVII). The reaction mixture is heated to a temperature between 100° C. and 150° C., and water removed from the reaction mixture using a Dean-Stark water separator. At least one equivalent of alcohol R3OH represented by formula (V); wherein R3 is a substituent as described above, but excluding hydrogen and salt-forming cations, is then added to the reaction mixture, and the thus prepared mixture heated to a reflux at a temperature between 100° C. and 150° C. to yield the formula (XXXVI) ester. The reaction may be graphically illustrated as follows: ##STR35## wherein R1, R2, R3, X, L, M, Q and R7 are as described above.
Sources & evidence
- ORD record
- ord-74cbeb8a51994e1895064ae76ed7eda9
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04923504
Reaction notes
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