Water → HCID 136017469, compound

HRID 1584156Notes

Reaction equation

HRID 1584156 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-7f96a12143aa4e1686632d38fdb92871
Source dataset
uspto-grants-1999_08
Patent number
US05932592

Reaction notes

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