Hydrochloric Acid → HCID 70021349, compound

HRID 1954037Notes

Reaction equation

HRID 1954037 reaction equation
C=C1CCCC1[O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:11]([O:13][CH3:14])=[O:12].N1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)C=CC=1.Cl>O>[C:26]1([CH2:25][C:9]2[C:8]([OH:7])=[C:17]([O:18][CH3:19])[CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])[CH2:27][CH2:28][CH2:29][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 23296053HCID 23296053, compound

Product 1

HCID 70021349HCID 70021349, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

12.7 g of methyl 3-(2-methylenecyclopentyloxy)-4-methoxybenzoate are treated with 50 ml of quinoline and the mixture is stirred at 190° C. for 1 h. After cooling, it is treated with water, adjusted to pH 3 using 2N HCl and extracted with ethyl acetate. The residue which remains after concentrating the solvent is chromatographed on a silica gel column using ethyl acetate/petroleum ether (4:6). The chromatographically pure fractions are concentrated and dried in a high vacuum. 10.2 g of the title compound are obtained as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. concentrationafter concentrating the solvent
  4. customis chromatographed on a silica gel column
  5. concentrationThe chromatographically pure fractions are concentrated
  6. customdried in a high vacuum

Sources & evidence

ORD record
ord-6448ff006e5b4b529607312efb8b4c9c
Source dataset
uspto-grants-2000_09
Patent number
US06121274

Reaction notes

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