Hydroxyamine hydrochloride → 3,7-Dichloroquinoline-8-carbonitrile

HRID 1980754Notes

Reaction equation

HRID 1980754 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=2[CH:13](Cl)Cl.Cl.[NH2:17]O.C([O-])=O.[Na+]>C(O)=O.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=2[C:13]#[N:17]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 130907853,7-Dichloro-8-(dichloromethyl)quinoline

Product 1

HCID 130907923,7-Dichloroquinoline-8-carbonitrileYield 78.5%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

28.1 parts by weight of the 3,7-dichloro-8-dichloromethylquinoline thus obtained, 6.95 parts by weight of hydroxylamine hydrochloride and 13.6 parts by weight of sodium formate in 200 ml of formic acid and 60 ml of water were stirred for 12 hours at 100° C., the reaction solution was poured onto ice, the precipitated solid was filtered off under suction, washed neutral with water and dried. 19 parts by weight of 3,7-dichloro-8-cyanoquinoline of melting point 222° C. were obtained. Yield: 78.5% of theory.

Workup

  1. additionthe reaction solution was poured onto ice
  2. filtrationthe precipitated solid was filtered off under suction
  3. washwashed neutral with water
  4. customdried

Sources & evidence

ORD record
ord-3ee7a7a981954f159dd551750df7ed5e
Source dataset
uspto-grants-1985_04
Patent number
US04511393

Reaction notes

Loading…