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

HRID 259855Notes

Reaction equation

HRID 259855 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2893b047d4754530ab361116f9b20703
Source dataset
uspto-grants-1996_06
Patent number
US05523407

Reaction notes

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