Dimethylformamide → 4-Chloro-7-methoxycinnoline hydrochloride

HRID 7485Notes

Reaction equation

HRID 7485 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:21])=O>>[ClH:21].[Cl:21][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178418974HCID 178418974, compound

Product 1

HCID 219910204-Chloro-7-methoxycinnoline hydrochlorideYield 97%

Procedure

The starting material 4-chloro-7-methoxycinnoline hydrochloride was obtained by heating a solution of 4-hydroxy-7-methoxycinnoline (352 mg, 2 mmol), (prepared as described in J. Chem. Soc. 1955, 2100), in thionyl chloride (3.5 ml) containing DMF (20 μl) at reflux, for 1 hour. After removing excess thionyl chloride by evaporation and azeotroping with toluene. The residue was triturated with ether, filtered off and washed with ether to give 4-chloro-7-methoxycinnoline hydrochloride as a yellow solid (450 mg, 97%).

Workup

  1. temperatureat reflux, for 1 hour
  2. customAfter removing excess thionyl chloride
  3. customby evaporation
  4. customazeotroping with toluene
  5. customThe residue was triturated with ether
  6. filtrationfiltered off
  7. washwashed with ether

Sources & evidence

ORD record
ord-6d4c3752ba7f4c5eae803cc519e25ef9
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Reaction notes

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