Water → HCID 136017469, compound

HRID 964589Notes

Reaction equation

HRID 964589 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:34][N:35]2[CH:39]=[N:38][CH:37]=[N:36]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][CH3:31])=[C:11]([O:32][CH3:33])[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]([CH2:34][N:35]2[CH:39]=[N:38][CH:37]=[N:36]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]([O:30][CH3:31])=[C:11]([O:32][CH3:33])[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 22097649HCID 22097649, compound

Product 1

HCID 136017469HCID 136017469, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3,4-diisopropoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (116.0 mg) in dichloromethane (2.5 ml), titanium tetrachloride (TiCl4) (288 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 chloroform-ethyl acetate (7:3, v/v) to yield 4-(3,4-dihydroxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (20.0 mg, 21%) having a melting point of 122° to 124° 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 chloroform-ethyl acetate (7:3

Sources & evidence

ORD record
ord-1bbb25549a9d4458b4daccf1eb4fdd20
Source dataset
uspto-grants-1998_06
Patent number
US05770602

Reaction notes

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