Thionyl Chloride → Methyl 4-chlorocinnoline-6-carboxylate

HRID 2079991Notes

Reaction equation

HRID 2079991 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][N:14]=[CH:13][C:12]2=O)=[O:8]>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[N:14][CH:13]=[C:12]2[Cl:3])=[O:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 67119550Methyl 4-oxo-1,4-dihydrocinnoline-6-carboxylate

Product 1

HCID 58387862Methyl 4-chlorocinnoline-6-carboxylateYield 82.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

Thionyl chloride (5 mL, 68.5 mmol) and N,N-dimethylformamide (3 drops) were added to 4-oxo-1,4-dihydro-cinnoline-6-carboxylic acid methyl ester (212 mg, 1.04 mol), and the solution was stirred for 1.15 hours under reflux. Toluene was added to the reaction mixture, which was then evaporated in vacuo. Ethyl acetate was added to the residue the organic layer was washed with an ice water, dried over anhydrous magnesium sulfate, then, evaporated in vacuo, and the title compound (192 mg, 0.862 mmol, 82.9%) was obtained. This was used in the next reaction without purification.

Workup

  1. temperatureunder reflux
  2. customwas then evaporated in vacuo
  3. additionEthyl acetate was added to the residue the organic layer
  4. washwas washed with an ice water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-dd52aa33e3f94ae09efc2ed988a1ed59
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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