Dicyclohexylcarbodiimide → 4-(2-Chlorophenyl)-3-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylcarbonyl)amino-6,8-dimethylquinoline

HRID 259859

Reaction equation

HRID 259859 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14](O)=[O:15])[CH2:6][CH2:5]2.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:34][C:35]1[CH:36]=[N:37][C:38]2[C:43]([C:44]=1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[Cl:51])=[CH:42][C:41]([CH3:52])=[CH:40][C:39]=2[CH3:53]>ClCCl>[Cl:51][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=1[C:44]1[C:43]2[C:38](=[C:39]([CH3:53])[CH:40]=[C:41]([CH3:52])[CH:42]=2)[N:37]=[CH:36][C:35]=1[NH:34][C:14]([C:7]1([CH3:17])[CH2:6][CH2:5][C:4]2[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([OH:1])[C:3]=2[CH3:18])[O:8]1)=[O:15]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 40634TroloxHCID 104465363-Amino-4-(2-chlorophenyl)-6,8-dimethylquinoline

Product 1

HCID 224039254-(2-Chlorophenyl)-3-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylcarbonyl)amino-6,8-dimethylquinolineYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (1.34 g) in dichloromethane (100 ml) was dropwise added DCC (945 mg) under stirring at a temperature of 0° C. The mixture was stirred at 0° C. for 15 minutes, and 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (1.04 g) was added thereto. Thus resulting mixture was further stirred at 0° C. for an hour and at room temperature for one night. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by a silica gel column chromatography with hexane-ethyl acetate (8:2,V/V), and then crystallized from acetone to give 4-(2-chlorophenyl)-3-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylcarbonyl)amino-6,8-dimethylquinoline (341 mg, 18.0%) as colorless prisms.

Workup

  1. stirringThe mixture was stirred at 0° C. for 15 minutes
  2. customThus resulting mixture
  3. stirringwas further stirred at 0° C. for an hour and at room temperature for one night
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by a silica gel column chromatography with hexane-ethyl acetate (8:2,V/V)
  7. customcrystallized from acetone

Sources & evidence

ORD record
ord-8a070a6c9bae4c88b1f263e0387c080f
Source dataset
uspto-grants-1996_06
Patent number
US05523407

Linked notes

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