Hydroxyamine hydrochloride → 2-Chloro-6-methoxy-3-quinolinecarboxaldehyde oxime

HRID 2073773Notes

Reaction equation

HRID 2073773 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][C:5]1[C:14]([CH:15]=O)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[CH:11]=2)[N:6]=1>O.C(O)C>[Cl:4][C:5]1[C:14]([CH:15]=[N:2][OH:3])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[CH:11]=2)[N:6]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 6890792-Chloro-6-methoxyquinoline-3-carbaldehyde

Product 1

HCID 24874202-Chloro-6-methoxy-3-quinolinecarboxaldehyde oximeYield 81.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 6.5 g hydroxylamine hydrochloride in 25 ml water was added to a suspension of 18.7 g 2-chloro-6-methoxy-3-quinolinecarboxaldehyde in 500 ml 95% ethanol. The mixture was stirred at room temperature for two hours and then heated at reflux for three hours. The reaction mixture was cooled to 0° C., filtered, and the filtrate concentrated to a volume of 200 ml. The product separated from solution to give 16.3 g 2-chloro-6-methoxy-3-quinolinecarboxaldehyde oxime, m.p. 195° C. (decompn.).

Workup

  1. temperatureheated
  2. temperatureat reflux for three hours
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated to a volume of 200 ml
  6. customThe product separated from solution

Sources & evidence

ORD record
ord-f5dbff4231e14eada58a54cbd705ed4b
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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