Triethylamine → 4-(2-Chlorophenyl)-3-(3,5-di-tert-butyl-4-hydroxybenzamido)-6,8-dimethylquinoline

HRID 259855

反応式

HRID 259855 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[CH:9][C:8]([CH3:19])=[CH:7][C:6]=2[CH3:20].[C:21]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:33]=1[OH:34])[C:28](O)=[O:29])([CH3:24])([CH3:23])[CH3:22].C(P(C#N)(CC)=O)C.C(N(CC)CC)C>CN(C=O)C.O>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:10]2[C:5](=[C:6]([CH3:20])[CH:7]=[C:8]([CH3:19])[CH:9]=2)[N:4]=[CH:3][C:2]=1[NH:1][C:28](=[O:29])[C:27]1[CH:31]=[C:32]([C:35]([CH3:36])([CH3:37])[CH3:38])[C:33]([OH:34])=[C:25]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:26]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 104465363-Amino-4-(2-chlorophenyl)-6,8-dimethylquinolineHCID 13586794Diethylphosphorylcyanide

生成物 1

HCID 152306244-(2-Chlorophenyl)-3-(3,5-di-tert-butyl-4-hydroxybenzamido)-6,8-dimethylquinoline収率 24.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (1.02 g), 3,5-di-tert-butyl-4-hydroxy benzoic acid (750 mg), diethylphosphoryl cyanide (DEPC) (587 mg) and N,N-dimethylformamide (100 mg) was dropwise added a solution of triethylamine (0.51 ml) in DMF (2 ml) under stirring at 0° C. The mixture was stirred at 0° C. for 30 minutes and at room temperature for one night. Then, the mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was concentrated after being washed with water and dried (MgSO4). The residue was purified by a silica gel column chromatography with hexane-ethyl acetate (85:15,V/V), and then crystallized from methanol to give 4-(2-chlorophenyl)-3-(3,5-di-tert-butyl-4-hydroxybenzamido)-6,8-dimethylquinoline (373 mg, 24.2%). Recrystallization from methanol gave colorless prisms of mp 127°-129° C.

後処理

  1. stirringThe mixture was stirred at 0° C. for 30 minutes and at room temperature for one night
  2. extractionextracted with ethyl acetate
  3. concentrationThe ethyl acetate layer was concentrated
  4. washafter being washed with water
  5. dry with materialdried (MgSO4)
  6. customThe residue was purified by a silica gel column chromatography with hexane-ethyl acetate (85:15,V/V)
  7. customcrystallized from methanol

出典と根拠

ORDレコード
ord-2893b047d4754530ab361116f9b20703
出典データセット
uspto-grants-1996_06
特許番号
US05523407

関連ノート

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