Water → HCID 135405017, compound

HRID 1648267Notes

Reaction equation

HRID 1648267 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:32][N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22]C(C)C)=[C:18]([O:26][CH3:27])[CH:17]=1)=[CH:13][C:12]([O:28][CH3:29])=[C:11]([O:30][CH3:31])[CH:10]=2)=[O:5])[CH3:2].O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:32][N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:26][CH3:27])[CH:17]=1)=[CH:13][C:12]([O:28][CH3:29])=[C:11]([O:30][CH3:31])[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 10767895HCID 10767895, compound

Product 1

HCID 135405017HCID 135405017, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,7-dimethoxy-4-(4-isopropoxy-3-methoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (55.6 mg) in dichloromethane (2 ml), titanium tetrachloride (TIC14) (125 mg) was added at 0° C., followed by stirring at the same temperature for 6 hours. The reaction mixture was poured over water and extracted with chloroform. The chloroform layer was washed by sequential additions of a saturated aqueous sodium hydrogen carbonate solution and water and then dried (MgSO4), after which the solvent was distilled off. The residual oily substance was subjected to silica gel column chromatography and eluted with ethyl acetate-chloroform (3:2, v/v)to yield 6,7-dimethoxy-4-(4-hydroxy-3-methoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (24.5 mg, 48%) which was then recrystallized from ethyl acetate-hexane having a melting point of 176° to 178° C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed by sequential additions of a saturated aqueous sodium hydrogen carbonate solution and water
  3. dry with materialdried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with ethyl acetate-chloroform (3:2, v/v)to

Sources & evidence

ORD record
ord-fc4ca7012de34df1889ec5b845cfbbb2
Source dataset
uspto-grants-1995_07
Patent number
US05436247

Reaction notes

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