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

HRID 615073Notes

Reaction equation

HRID 615073 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[CH2:13]Cl.Cl.[NH2:16]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:16]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 13090784HCID 13090784, compound

Product 1

HCID 130907923,7-Dichloroquinoline-8-carbonitrile

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

28.1 parts of 3,7-dichloro-8-chloromethylquinoline (Example 1), 6.95 parts of hydroxylamine hydrochloride and 13.6 parts of sodium formate in 200 ml of formic acid and 60 ml of water were stirred at 100° C. for 12 hours. The reaction solution was poured onto ice and the precipitated solid was filtered off with suction, washed neutral with water and dried. 19 parts of 3,7-dichloro-8-cyanoquinoline of melting point 222° C. were obtained. The yield corresponds to 78.5% of theory.

Workup

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

Sources & evidence

ORD record
ord-e484d41706ac45d68675df1294a7149d
Source dataset
uspto-grants-1985_02
Patent number
US04497651

Reaction notes

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