Sulfuric Acid → 4-[4-Methyl-5-(2-methyl-quinolin-6-yl)-4H-[1,2,4]triazol-3-yl]-butyraldehyde

HRID 33227Notes

Reaction equation

HRID 33227 reaction equation
[O:1]1CCCO[CH:2]1[CH2:7][CH2:8][CH2:9][C:10]1[N:11]([CH3:26])[C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[C:20]([CH3:25])[CH:19]=[CH:18]3)=[N:13][N:14]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O>[CH3:26][N:11]1[C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[C:20]([CH3:25])[CH:19]=[CH:18]3)=[N:13][N:14]=[C:10]1[CH2:9][CH2:8][CH2:7][CH:2]=[O:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 693120036-[5-(3-[1,3]Dioxan-2-yl-propyl)-4-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-quinoline

Product 1

HCID 865941724-[4-Methyl-5-(2-methyl-quinolin-6-yl)-4H-[1,2,4]triazol-3-yl]-butyraldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-[5-(3-[1,3]Dioxan-2-yl-propyl)-4-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-quinoline (109 mg, 0.31 mmol) was heated in water (20 ml) and concentrated sulphuric acid (0.5 ml) at 100° C. for 3 h. The mixture was cooled to room temperature, basified with solid sodium bicarbonate and extracted with dichloromethane (3×50 ml). The combined organic portions were dried (Na2SO4), filtered and evaporated to give the desired compound as an off-white solid (76 mg, 84%).

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. dry with materialThe combined organic portions were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-69c2601b920347269cf7714d435e6859
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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