3-Hydroxybenzaldehyde → HCID 10245656, compound

HRID 2248899Notes

Reaction equation

HRID 2248899 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.[OH:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([O:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:16](/[CH:17]=[CH:12]/[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)(=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7918Acetic AnhydrideHCID 1383957-Chloro-2-methylquinoline

Product 1

HCID 10245656HCID 10245656, compound

Procedure

A solution of 7-chloroquinaldine (10 g, 56.3 mmol) and 3-hydroxybenzaldehyde (6.87 g, 56.3 mmol) in 25 ml of acetic anhydride is heated at 130° C. for 16 hours. The reaction mixture is concentrated and the beige solid recrystallized from hexane-ethyl acetate to afford (E)-3-(7-chloro-2-quinolinylethenyl)phenyl acetate which is used directly in the next step.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe beige solid recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-9e9328c73894423ca8c9725edd44a663
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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