Sulfuric Acid → 2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxymethyl]-propane-1,3-diol

HRID 228988Notes

Reaction equation

HRID 228988 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([CH3:25])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N=C=NN=NN=C=NCC)C.S(=O)(=O)(O)O.[OH-].[Na+].CC1(C)[O:70][CH2:69][CH:68]([CH2:71]O)[CH2:67][O:66]1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:71][CH:68]([CH2:69][OH:70])[CH2:67][OH:66])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([CH3:25])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolHCID 86605188DiethylazocarbodiimideHCID 1358548286-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol2×

Product 1

HCID 577565932-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxymethyl]-propane-1,3-diolYield 45.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol (compound 352) (50 mg) and triphenylphosphine (158 mg) were dissolved in tetrahydrofuran (1 ml) to prepare a solution. A solution of diethylazocarbodiimide (105 mg) in (2,2-dimethyl[1,3]dioxan-5-yl)-methanol (27 mg) and tetrahydrofuran (0.2 ml) was added to the solution, and the mixture was stirred at room temperature for 5 hr. A 1 N aqueous sulfuric acid solution (1 ml) was then added to the reaction solution, and the mixture was stirred at room temperature overnight. The reaction solution was made alkaline by the addition of 1 N sodium hydroxide, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (29 mg, yield 45%).

Workup

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-1e29acd55e944b2eaf02a3340412ba63
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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