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

HRID 2379480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2379480
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 152306244-(2-Chlorophenyl)-3-(3,5-di-tert-butyl-4-hydroxybenzamido)-6,8-dimethylquinolineAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-75204cccb2f74fafa026fa5af2ebb21d
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05362742

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