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

HRID 259862ノート

反応式

HRID 259862 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 30 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.

後処理

  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

出典と根拠

ORDレコード
ord-fb25bdc760bd432b899f56148d3c6010
出典データセット
uspto-grants-1996_06
特許番号
US05523407

反応ノート

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