Acetic Anhydride → 3-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]benzaldehyde

HRID 1198528Notes

Reaction equation

HRID 1198528 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[CH:13](=O)[C:14]1[CH:21]=[CH:20][CH:19]=[C:16]([CH:17]=[O:18])[CH:15]=1.C(OC(=O)C)(=O)C.CCCCCC>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=[O:18])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8058HexaneHCID 34777IsophthalaldehydeHCID 1383957-Chloro-2-methylquinoline

Product 1

HCID 100173053-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred solution of 7-chloroquinaldine [J. Org. Chem. 42, 911 (1977)] (4.46 g, 25 mmol) and isophthalaldehyde (5.02 g, 37.5 mmol) in acetic anhydride (7.1 ml, 75 mmol) and xylene (25 ml) was heated under reflux for 7 hours. Crystals formed on cooling. Hexane (25 ml) was added slowly to give crude product, m.p. 146°-150°.

Workup

  1. temperatureunder reflux for 7 hours
  2. customCrystals formed
  3. temperatureon cooling
  4. customto give crude product, m.p. 146°-150°

Sources & evidence

ORD record
ord-c84e116f4dac4b9cb1e737deb526ed82
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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