3-Hydroxybenzaldehyde → HCID 2953702, compound

HRID 1088447Notes

Reaction equation

HRID 1088447 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[N:10]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:11]=1[CH3:12].[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:21]([O:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:12][C:11]2[CH:13]=[CH:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 70602-MethylquinolineHCID 7918Acetic Anhydride

Product 1

HCID 2953702HCID 2953702, compound

Procedure

A solution of 3-hydroxybenzaldehyde (25 g) and quinaldine (28 ml) in acetic anhydride (150 ml) was heated overnight at 130° cooled and evaporated in vacuo. Purification of the residue by flash chromatography using 35% ether in hexane to 45% ether in hexane afforded the title quinoline compound after recrystallization from ether/hexane, m.p. 86-87°.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-4a16ece1133f4026beac377c492ffd27
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

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