Ammonia → 7-Amino-3-chloroquinoline-8-carbonitrile

HRID 1980753Notes

Reaction equation

HRID 1980753 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)[C:6]=2[C:13]#[N:14].[NH3:15]>CO>[NH2:15][C:7]1[C:6]([C:13]#[N:14])=[C:5]2[C:10]([CH:11]=[C:2]([Cl:1])[CH:3]=[N:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 130907923,7-Dichloroquinoline-8-carbonitrile

Product 1

HCID 132065287-Amino-3-chloroquinoline-8-carbonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

110 g of 3,7-dichloro-8-cyanoquinoline, 500 ml of methanol and 500 ml of liquid ammonia were heated at 150° C. for 10 hours in an autoclave. The pressure was let down, after which the discharged mixture was filtered under suction, and the solid was recrystallized from methylglycol, in the presence of active charcoal. 54 g of 7-amino-3-chloro-8-cyanoquinoline of melting point 246° C. were obtained. Yield: 53% of theory.

Workup

  1. filtrationafter which the discharged mixture was filtered under suction
  2. customthe solid was recrystallized from methylglycol, in the presence of active charcoal

Sources & evidence

ORD record
ord-cb67630bef864498b6d418c5300bfc03
Source dataset
uspto-grants-1985_04
Patent number
US04511393

Reaction notes

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