Hydroxyamine hydrochloride → 2-Chloroquinoline-3-carbonitrile

HRID 2413152

Reaction equation

HRID 2413152 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[NH2:15]O>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[C:11]([C:12]#[N:15])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 6909582-Chloro-3-quinolinecarboxaldehyde

Product 1

HCID 115646012-Chloroquinoline-3-carbonitrileYield 71.1%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture was prepared from 10 g of 2-chloro-3-quinolinecarboxaldehyde, 5.2 g of hydroxylamine hydrochloride and 100 ml of phosphoryl chloride and heated with a heat lamp. The mixture was heterogeneous until the temperature reached 90° C. and there was no noticeable exotherm or gas evolution. After heating at reflux for 30 minutes, the mixture was cooled for 16 hours. It was then quenched in 700 ml of water. The tan solid which formed was separated by filtration and dried to give 7 g of crude 2-chloro-3-cyanoquinoline.

Workup

  1. temperatureheated with a heat lamp
  2. customreached 90° C.
  3. temperatureAfter heating
  4. temperatureat reflux for 30 minutes
  5. temperaturethe mixture was cooled for 16 hours
  6. customIt was then quenched in 700 ml of water
  7. customThe tan solid which formed
  8. customwas separated by filtration
  9. customdried

Sources & evidence

ORD record
ord-8445ec0f90394645a7e7b4ce05565a26
Source dataset
uspto-grants-1985_01
Patent number
US04496569

Linked notes

Loading…