Thionyl Chloride → 4-Chloro-6,7-dimethoxycinnoline hydrochloride

HRID 7463Notes

Reaction equation

HRID 7463 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.S(Cl)([Cl:18])=O>CN(C=O)C>[ClH:18].[Cl:18][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178419049HCID 178419049, compound

Product 1

HCID 219910134-Chloro-6,7-dimethoxycinnoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

The starting material, 4-chloro-6,7-dimethoxycinnoline hydrochloride was obtained by heating a solution of 4-hydroxy-6,7-dimethoxycinnoline (1 g, 4.8 mmol) in thionyl chloride (20 ml) containing DMF (2 drops) at reflux for 3 hours. After cooling and evaporating the excess thionyl chloride, the solid was triturated with ether and filtered to give 4-chloro-6,7-dimethoxycinnoline hydrochloride (1.2 g, quantitative).

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling
  3. customevaporating the excess thionyl chloride
  4. customthe solid was triturated with ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4a0bf0cfcfb549828ce701f9b04db88c
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Reaction notes

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