Water → HCID 136023069, compound

HRID 1648269Notes

Reaction equation

HRID 1648269 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:36][N:37]2[CH:41]=[N:40][CH:39]=[N:38]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]C(C)C)[CH:17]=1)=[CH:13][C:12]([O:30]C(C)C)=[C:11]([O:34][CH3:35])[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]([CH2:36][N:37]2[CH:41]=[N:40][CH:39]=[N:38]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:26])[CH:17]=1)=[CH:13][C:12]([OH:30])=[C:11]([O:34][CH3:35])[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 22097619HCID 22097619, compound

Product 1

HCID 136023069HCID 136023069, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3,4-diisopropoxyphenyl)-6-isopropoxy-7-methoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (96.0 rag) in dichloromethane (1.0 ml), titanium tetrachloride (TICl4) (316 mg) was added at 0° C., followed by stirring at the same temperature for 10 hours. The reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate 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-methanol (10:1, v/v) to yield 4-(3,4-dihydroxyphenyl)-6-hydroxy-7-methoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (19.0 mg, 26%) having a melting point of 264° to 266° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate 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-methanol (10:1

Sources & evidence

ORD record
ord-46efc2bc44ee42aa811707dd3854bd26
Source dataset
uspto-grants-1995_07
Patent number
US05436247

Reaction notes

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