Water → HCID 135405017, compound

HRID 862641Notes

Reaction equation

HRID 862641 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:7]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([O:32]C(C)C)=[C:28]([O:36][CH3:37])[CH:27]=1.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:7]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([O:36][CH3:37])[CH:27]=1

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

Titanium tetrachloride (TiCl4)(125 mg) was added at 0° C. to a solution of ethyl 6,7-dimethoxy-4-(4-isopropoxy-3-methoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (55.6 mg) in dichloromethane (2 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 carbonate 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(3/2, v/v) gave ethyl 6,7-dimethoxy-4-(4-hydroxy-3-methoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (24.5 mg, 48%) which was then recrystallized from ethyl acetate-hexane. mp. 176°-178° C.

Workup

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

Sources & evidence

ORD record
ord-89deea00a9464ba4a5e2e3d972428689
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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