Hydrochloric Acid → 3-(pyridin-3-yl)-1H-quinolin-4-one

HRID 69049Notes

Reaction equation

HRID 69049 reaction equation
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[OH-:19].[Na+]>CN(C=O)C>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:4]2[C:3](=[O:19])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66961193HCID 66961193, compound

Product 1

HCID 669611103-(pyridin-3-yl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2N Hydrochloric acid (10 ml) was added to a DMF solution (5 ml) of 4-chloro-(3-pyridin-3-yl)quinoline (0.51 g), and the mixture was stirred at 80° C. for 1 hour. After the reaction mixture was cooled to room temperature, 2N sodium hydroxide aqueous solution (10 ml) was added dropwise under ice cooling. The mixture was stirred. The precipitated insoluble matter was separated, washed with water and ether, and dried to give the title compound (0.35 g) as a pale whitish purple powder.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred
  3. customThe precipitated insoluble matter was separated
  4. washwashed with water and ether
  5. customdried

Sources & evidence

ORD record
ord-9a09dd03ff5d4647a5b5af28f48ea195
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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