Clonidine → 1H-Imidazol-2-amine, 4,5-dihydro-N-(2,6-dichlorophenyl)-1-(2-quinolinylcarbonyl)-
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[NH:22][C:23]1[NH:24][CH2:25][CH2:26][N:27]=1>O1CCCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([N:27]1[CH2:26][CH2:25][N:24]=[C:23]1[NH:22][C:16]1[C:17]([Cl:21])=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14])=[O:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2.85 g (16.5 millimoles) of quinoline-2-carboxylic acid are dissolved in 200 ml of absolute tetrahydrofuran, 2.7 g (16.5 millimoles) of N,N'-carbonyl-diimidazole are added and the mixture is stirred for 45 minutes at room temperature. A solution of 3.75 g (16.5 millimoles) of 2-(2',6'-dichlorophenylamino)-2-imidazoline in 75 ml of absolute tetrahydrofuran is then added dropwise and the batch is stirred overnight. Thereafter, the reaction solution is freed from solvent on a rotary evaporator and the oily residue is introduced into 200 ml of an 0.5% strength sodium bicarbonate solution. The crystalline crude product (5.2 g) is filtered off and recrystallized from N,N-dimethylacetamide/isopropanol, and the crystals are washed with cold isopropanol. 3.3 g of 1-(quinolin-2-oyl)-2-(2',6'-dichlorophenylamino)-2-imidazoline are obtained, melting point 197°-198° C.
Workup
- stirringthe batch is stirred overnight
- customThereafter, the reaction solution is freed from solvent on a rotary evaporator
- additionthe oily residue is introduced into 200 ml of an 0.5% strength sodium bicarbonate solution
- filtrationThe crystalline crude product (5.2 g) is filtered off
- customrecrystallized from N,N-dimethylacetamide/isopropanol
- washthe crystals are washed with cold isopropanol
Sources & evidence
- ORD record
- ord-7a7da36a878b421a8f195b5d7cdb11ad
- Source dataset
- uspto-grants-1983_06
- Patent number
- US04389403
Reaction notes
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