Water → HCID 136017469, compound

HRID 862642Notes

Reaction equation

HRID 862642 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[C:17]([CH2:29][N:30]3[CH:34]=[N:33][CH:32]=[N:31]3)[C:16]=2[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:8]=[CH:9][C:10]=1[O:11]C(C)C)(C)C.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:4][C:5]1[CH:6]=[C:7]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[C:17]([CH2:29][N:30]3[CH:34]=[N:33][CH:32]=[N:31]3)[C:16]=2[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:8]=[CH:9][C:10]=1[OH:11]

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

Titanium tetrachloride (TiCl4)(288 mg) was added at 0° C. to a solution of ethyl 4-(3,4-diisopropoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (116.0 mg) in dichloromethane (2.5 ml), and the mixture was stirred at the same temperature for 6 hours. The reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed with a saturated aqueous sodium bicarbonate solution and water, and dried over magnesium sulfate. The solvent was evaporated. The residual oil was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate/chloroform(7/3, v/v) gave ethyl 4-(3,4-dihydroxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (20.0 mg, 21%). mp. 122°-124° C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with a saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. washThe fractions eluted with ethyl acetate/chloroform(7/3

Sources & evidence

ORD record
ord-01c81e2aa2d043d0ac80d0fd9017639f
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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