Dicyclohexylcarbodiimide → HCID 15230625, compound

HRID 259856Notes

Reaction equation

HRID 259856 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:34][C:35]1[CH:36]=[N:37][C:38]2[C:43]([C:44]=1[C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[C:47]([O:53][CH3:54])[C:46]=1[O:55][CH3:56])=[CH:42][C:41]([Cl:57])=[CH:40][CH:39]=2>ClCCl>[C:15]([C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:13]=1[OH:14])[C:8]([NH:34][C:35]1[CH:36]=[N:37][C:38]2[C:43]([C:44]=1[C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[C:47]([O:53][CH3:54])[C:46]=1[O:55][CH3:56])=[CH:42][C:41]([Cl:57])=[CH:40][CH:39]=2)=[O:10])([CH3:17])([CH3:16])[CH3:18]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 15035245HCID 15035245, compound

Product 1

HCID 15230625HCID 15230625, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,5-di-tert-butyl-4-hydroxybenzoic acid (220 mg) in dichloromethane (20 ml) was dropwise added dicyclohexylcarbodiimide (DCC) (180 mg) under stirring at 0° C. The mixture was stirred at 0° C. for 15 minutes. Then, 3-amino-6-chloro-4-(2,3,4-trimethoxyphenyl) quinoline (250 mg) was added to this mixture. The resultant mixture was stirred at 0° C. for an hour and at room temperature for two days. After the residue was filtered off, the filtrate was diluted with water and extracted with dichloromethane. The dichloromethane layer was washed with an aqueous sodium hydroxide solution, diluted with hydrochloric acid and water in this order and dried (MgSO4). The solvent was removed and the residue was purified by a silica gel column chromatography with hexane-ethyl acetate (3:1, V/V), and then crystallized from isopropyl ether to obtain 3-(3,5-di-tert-butyl-4-hydroxybenzamido)-6-chloro-4-(2,3, 4-trimethoxyphenyl) quinoline (199 mg, 47.6%).

Workup

  1. stirringThe mixture was stirred at 0° C. for 15 minutes
  2. filtrationAfter the residue was filtered off
  3. additionthe filtrate was diluted with water
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer was washed with an aqueous sodium hydroxide solution
  6. additiondiluted with hydrochloric acid and water in this order
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed
  9. customthe residue was purified by a silica gel column chromatography with hexane-ethyl acetate (3:1, V/V)
  10. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-cf223c94507e484e8d5ca5d6c00e5f93
Source dataset
uspto-grants-1996_06
Patent number
US05523407

Reaction notes

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