Dicyclohexylcarbodiimide → 3-(3,5-Di-tert-butyl-4-hydroxycinnamoylamino)-4-(2-chlorophenyl)-6,8-dimethylquinoline

HRID 2379487Notes

Reaction equation

HRID 2379487 reaction equation
ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[C:26]([C:30]1[CH:31]=[C:32]([CH:38]=[C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:40]=1[OH:41])[CH:33]=[CH:34][C:35](O)=[O:36])([CH3:29])([CH3:28])[CH3:27].[NH2:46][C:47]1[CH:48]=[N:49][C:50]2[C:55]([C:56]=1[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[Cl:63])=[CH:54][C:53]([CH3:64])=[CH:52][C:51]=2[CH3:65]>CN(C=O)C>[C:42]([C:39]1[CH:38]=[C:32]([CH:31]=[C:30]([C:26]([CH3:28])([CH3:27])[CH3:29])[C:40]=1[OH:41])[CH:33]=[CH:34][C:35]([NH:46][C:47]1[CH:48]=[N:49][C:50]2[C:55]([C:56]=1[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[Cl:63])=[CH:54][C:53]([CH3:64])=[CH:52][C:51]=2[CH3:65])=[O:36])([CH3:44])([CH3:45])[CH3:43]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acidHCID 104465363-Amino-4-(2-chlorophenyl)-6,8-dimethylquinoline

Product 1

HCID 537989013-(3,5-Di-tert-butyl-4-hydroxycinnamoylamino)-4-(2-chlorophenyl)-6,8-dimethylquinolineYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (154 mg) and dicyclohexylcarbodiimide (272 mg) were added to a solution of 3,5-di-tert-butyl-4-hydroxycinnamic acid (331 mg) in DMF (5 ml). The mixture was stirred at room temperature for minutes, and then, 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (288 mg) was added thereto. The resultant mixture was further stirred at room temperature for 24 hours. The insoluble materials were filtered off, while the filtrate was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was removed, and the residue was purified by a silica gel chromatography with benzene-acetone (9:1), then, crystallized from isopropyl ether to give 3-(3,5-di-tert-butyl-4-hydroxycinnamoylamino)-4-(2-chlorophenyl)-6,8-dimethylquinoline (257 mg, 47.5%) as colorless needles.

Workup

  1. filtrationThe insoluble materials were filtered off, while the filtrate
  2. additionwas diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed
  7. customthe residue was purified by a silica gel chromatography with benzene-acetone (9:1)
  8. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-98e97a8dae82496c9ce64dca0b50cc24
Source dataset
uspto-grants-1994_11
Patent number
US05362742

Reaction notes

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