Quinoline → HCID 70144486, compound

HRID 2301003Notes

Reaction equation

HRID 2301003 reaction equation
C[C:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:4][CH:3]=1.N1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]C=1.[CH3:22]CCCCC.[C:28]([O:31]CC)(=[O:30])C>>[C:28](=[O:30])([O:11][C:8]([CH:5]1[CH2:6][CH2:7][CH:2]=[C:3]([CH3:22])[CH2:4]1)([CH3:9])[CH3:10])[O:31][C:19]1[CH:20]=[CH:21][C:16]([CH:15]=[CH2:14])=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 7047QuinolineHCID 443162(L)-alpha-TerpineolHCID 21226206Ethyl acetate hexane

Product 1

HCID 70144486HCID 70144486, compoundYield 32%

Procedure

The resulting mixture above was used directly without treatment and the same reaction system was used continuously. The dropping funnel on the flask was charged of α-terpineol (7.7 g) and quinoline (6.5 g). The formed solution was added dropwise to the reaction system at room temperature over vigorous stirring. The mixture was stirred over night and a white salt gradually precipitated. The salt was separated and the organic phase was washed with 2 N HCl and water until all pyridine and quinoline were neutralized and washed out. The organic phase was separated, washed with sodium bicarbonate and sodium bisulfite solution, and then dried over anhydrous magnesium sulfate. The column chromatography of the products on silica gel with 10:1 hexane/ethyl acetate gave 32% yield of the product as a colorless viscous liquid. FT-IR (neat): 2925, 1757, 1508, 1446, 1376, 1264, 1214, 1157, 1123, 1018, 990, 903, 840, 809 cm−1. 1H NMR (CDCl3): δ7.40 (d, 2H, aromatic), 7.12 (d, 2H, aromatic), 6.69 (dd, 1H, ═CH, aromatic), 5.70 (dd, 1H, ═CH2), 5.38 (m, 1H, ═CH), 5.24 (dd, 1H, ═CH2), 2.19-1.83 (m, 6H, CH2), 1.66 (s, 3H, CH3) 1.54 (s, 3H, CH3), 1.51 (s, 3H, CH3), 1.44-1.25 (m, 1H, CH) ppm.

Workup

  1. additionThe formed solution was added dropwise to the reaction system at room temperature over vigorous stirring
  2. customa white salt gradually precipitated
  3. customThe salt was separated
  4. washthe organic phase was washed with 2 N HCl and water until all pyridine and quinoline
  5. washwashed out
  6. customThe organic phase was separated
  7. washwashed with sodium bicarbonate and sodium bisulfite solution
  8. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-0889721edded49f59c11923fb37c70ec
Source dataset
uspto-grants-2002_12
Patent number
US06498260B2

Reaction notes

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