Hydroxyamine hydrochloride → 2-Oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 2413148Notes

Reaction equation

HRID 2413148 reaction equation
Cl.[NH2:2]O.[CH:4]([O-:6])=O.[Na+].ClC1[C:18]([CH:19]=O)=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1>C(O)=O>[C:19]([C:18]1[C:4](=[O:6])[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)#[N:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 6909582-Chloro-3-quinolinecarboxaldehydeHCID 2723810Sodium Formate

Product 1

HCID 27645772-Oxo-1,2-dihydroquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture was prepared from 6 liters of 97% formic acid, 300 g of hydroxylamine hydrochloride, 500 g of sodium formate, and 700 g of 2-chloro-3-quinolinecarboxaldehyde and this mixture was heated to reflux (110° C.). The resulting solution was then maintained at 110° C. for 18 hours. The solution was then cooled and the solid which crystallized was separated by filtration and then successively washed twice with water, once with ethanol and once with methylene chloride to give 3-cyano-2(1H)-quinolinone.

Workup

  1. temperaturethis mixture was heated
  2. temperatureThe resulting solution was then maintained at 110° C. for 18 hours
  3. temperatureThe solution was then cooled
  4. customthe solid which crystallized
  5. customwas separated by filtration
  6. washsuccessively washed twice with water, once with ethanol and once with methylene chloride

Sources & evidence

ORD record
ord-512febfda5f94ae2a0845604c25fbe68
Source dataset
uspto-grants-1985_01
Patent number
US04496569

Reaction notes

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