O-Xylene → 3-(2-(7-Chloroquinolin-2-yl)vinyl)benzaldehyde

HRID 1639354Notes

Reaction equation

HRID 1639354 reaction equation
C1(C)C(C)=CC=CC=1.[Cl:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([CH3:20])=[N:17]2)=[CH:12][CH:11]=1.[CH:21](=O)[C:22]1[CH:29]=[CH:28][CH:27]=[C:24]([CH:25]=[O:26])[CH:23]=1.C(OC(=O)C)(=O)C>CCCCCC>[Cl:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([CH:20]=[CH:21][C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[CH:25]=[O:26])=[N:17]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 7918Acetic AnhydrideHCID 34777IsophthalaldehydeHCID 1383957-Chloro-2-methylquinoline

Product 1

HCID 533948533-(2-(7-Chloroquinolin-2-yl)vinyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 15 liters of xylene preheated to 100° were added sequentially 7-chloroquinaldine (3 kg, 16.9 moles; see C. M. Leir, J. Org. Chem., 42, 911-913 (1977)), isophthalaldehyde (3.4 kg, 25.3 moles), and acetic anhydride (4.69 liters, 5.07 kg, 49.7 moles). The mixture was heated at reflux for about 8 to 9 hours and then cooled to room temperature. Hexane (16 liters) was added and the resultant precipitate was collected by filtration. Recrystallization from ethyl acetate yielded pure title compound (67%).

Workup

  1. custompreheated to 100°
  2. temperatureThe mixture was heated
  3. temperatureat reflux for about 8 to 9 hours
  4. filtrationthe resultant precipitate was collected by filtration
  5. customRecrystallization from ethyl acetate yielded pure title compound (67%)

Sources & evidence

ORD record
ord-75c3215fb89649f7a54207f5d2cfbd5c
Source dataset
uspto-grants-1989_11
Patent number
US04883878

Reaction notes

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