3-Methoxybenzaldehyde → (E)-3-(2-(7-chloroquinolin-2-yl)ethenyl)anisole

HRID 1088469Notes

Reaction equation

HRID 1088469 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH3:22])=[N:19]2)=[CH:14][CH:13]=1>C(OC(=O)C)(=O)C>[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18](/[CH:22]=[CH:6]/[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=[CH:9][CH:8]=3)=[N:19]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 115693-MethoxybenzaldehydeHCID 1383957-Chloro-2-methylquinoline

Product 1

HCID 22163088(E)-3-(2-(7-chloroquinolin-2-yl)ethenyl)anisole

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
110 °C

Procedure

7.1 mL of 3-methoxybenzaldehyde (58 mmoles), 9.953 g of 7-chloroquinaldine (56 mmoles) and 50 mL of acetic anhydride were mixed together and heated at 110° C. for 16 hours. After hydrolysis on ice, the product was extracted with ethyl acetate, washed with 5% sodium bicarbonate and brine and partially purified by flash chromatography using 10% ethyl acetate in hexane. Recrystallisation from ether: hexane yielded the title compound.

Workup

  1. customAfter hydrolysis on ice
  2. extractionthe product was extracted with ethyl acetate
  3. washwashed with 5% sodium bicarbonate and brine
  4. custompartially purified by flash chromatography
  5. customRecrystallisation from ether

Sources & evidence

ORD record
ord-d067cb4f58a841b4b0a746e452b83984
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

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