Water → HCID 136023069, compound

HRID 862643Notes

Reaction equation

HRID 862643 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:29][CH3:30])=[C:22]([O:25]C(C)C)[CH:23]=3)[N:18]=[C:17]([CH2:31][N:32]3[CH:36]=[N:35][CH:34]=[N:33]3)[C:16]=2[C:37]([O:39][CH2:40][CH3:41])=[O:38])[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:29][CH3:30])=[C:22]([OH:25])[CH:23]=3)[N:18]=[C:17]([CH2:31][N:32]3[CH:36]=[N:35][CH:34]=[N:33]3)[C:16]=2[C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:8]=[CH:9][C:10]=1[OH:11]

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

Titanium tetrachloride (TiCl4)(316 mg) was added at 0° C. to a solution of ethyl 4-(3,4-diisopropoxyphenyl)-6-isopropoxy-7-methoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (96.0 mg) in dichloromethane (1.0 ml), and the mixture was stirred at the same temperature for 10 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate 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/methanol (10/1, v/v) gave ethyl 4-(3,4-dihydroxyphenyl)-6-hydroxy-7-methoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (19.0 mg, 26%). mp. 264°-266° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate 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/methanol (10/1

Sources & evidence

ORD record
ord-c893425f192d4517aa68f0fa9c2675bd
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

Loading…