Quinoline → HCID 23296051, compound

HRID 1954035Notes

Reaction equation

HRID 1954035 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13]CC(C)=C.C(OCC)(=O)C.N1[C:33]2[C:28](=[CH:29]C=CC=2)[CH:27]=CC=1>>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[C:4]([OH:13])[C:5]=1[CH2:29][C:28]([CH3:33])=[CH2:27]

Participants

4

Reactant 3

HCID 7047QuinolineHCID 8857Ethyl AcetateHCID 23296057HCID 23296057, compound

Product 1

HCID 23296051HCID 23296051, compound

Conditions

Temperature
185 °C

Procedure

20 g of methyl 4-methoxy-3-(2-methyl-2-propenyloxy)benzoate are dissolved in 60 ml of quinoline and the mixture is heated at 180-190° C. for 2 h. After cooling, it is treated with ethyl acetate and the quinoline is extracted using 2N HCl. The organic phase is washed a further 2 times with water and concentrated. The oily residue is chromatographed on a silica gel column using ethyl acetate/petroleum ether (4:6). The chromatographically pure fractions are combined, concentrated and dried in a high vacuum. 15.6 g of the title compound are obtained as a pale yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionthe quinoline is extracted
  3. washThe organic phase is washed a further 2 times with water
  4. concentrationconcentrated
  5. customThe oily residue is chromatographed on a silica gel column
  6. concentrationconcentrated
  7. customdried in a high vacuum

Sources & evidence

ORD record
ord-e9f9b6f73970403db1776cf9970662d2
Source dataset
uspto-grants-2000_09
Patent number
US06121274

Reaction notes

Loading…