Hydrochloric Acid → 6,8-Dichloro-2,7-naphthyridin-1(2H)-one

HRID 1034942Notes

Reaction equation

HRID 1034942 reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH:11]=[CH:12][N:13]2[CH2:17]CCC2)[C:3]=1C#N.Cl.[OH2:19]>>[Cl:10][C:8]1[CH:7]=[C:6]2[C:3](=[C:2]([Cl:1])[N:9]=1)[C:17](=[O:19])[NH:13][CH:12]=[CH:11]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 76664879HCID 76664879, compound

Product 1

HCID 580937976,8-Dichloro-2,7-naphthyridin-1(2H)-one

Procedure

A suspension 2,6-dichloro-4-(2-(pyrrolidin-1-yl)vinyl)nicotinonitrile (2 g, 7.457 mmol) in 6 mL of conc-HCl is stirred at 60° C. for 6 hours and stirred at room temperature for 1 hour. The reaction mixture is added to 50 mL of water and the precipitate is collected by filtration and washed with water and ether to give 1.4 g of 6,8-dichloro-2,7-naphthyridin-1(2H)-one as a crude product (pale yellow solid). The dichloro compound was used for the reaction transformations without any further purification.

Workup

  1. filtrationthe precipitate is collected by filtration
  2. washwashed with water and ether

Sources & evidence

ORD record
ord-1f3f6dfb71a6466e9ea718dc0fe9cafa
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Reaction notes

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