Dimethylformamide → 4-Chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline

HRID 7466Notes

Reaction equation

HRID 7466 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:26])=O>>[Cl:26][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178418847HCID 178418847, compound

Product 1

HCID 107070484-Chloro-6-methoxy-7-(2-methoxyethoxy)cinnolineYield 74%

Procedure

The starting material 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline was obtained by heating a solution of 4-hydroxy-6-methoxy-7-(2-methoxyethoxy)cinnoline (7.8 g, 0.031 mol) in thionyl chloride (130 ml) containing DMF (0.8 ml) at 80° C. for 2 hours. After dilution with toluene, the mixture was evaporated to dryness. The resulting solid was filtered off, washed with ether, and then dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate solution and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/ethyl acetate (1/9) as eluent to give 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (6.2 g, 74%).

Workup

  1. customAfter dilution with toluene, the mixture was evaporated to dryness
  2. filtrationThe resulting solid was filtered off
  3. washwashed with ether
  4. dissolutiondissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialbrine, dried (MgSO4)
  7. customthe solvent evaporated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2038e2c80790471a92c60a139f03a652
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Reaction notes

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