N-chlorosuccinamide → HCID 131731039, compound

HRID 2039643Notes

Reaction equation

HRID 2039643 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([OH:14])=[O:13])[N:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[CH:6]=[CH:5]2.[Cl:19]N[C:21](=O)[CH2:22]CC(N)=O>CN(C)C=O.C(OCC)(=O)C>[CH2:21]([NH+:8]([CH2:7][CH3:15])[CH2:9][CH3:10])[CH3:22].[NH2:1][C:2]1[C:3]([Cl:19])=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([O-:14])=[O:13])[N:8]=[C:7]([C:15]([F:18])([F:16])[F:17])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 15238416N-chlorosuccinamideHCID 57855904HCID 57855904, compound

Product 1

HCID 131731039HCID 131731039, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

6-Amino-2-trifluoromethyl-quinoline-7-carboxylic acid (0.50 g, 1.952 mmol is dissolved in dimethyl formamide (10 ml) and treated with N-chlorosuccinamide (0.26 g, 1.952 mmol) and the mixture warmed to 80° C. After 1 hr the reaction is complete as shown by LC/MS analysis. The reaction mixture is cooled, diluted with ethyl acetate, and then washed successively with water and brine. The organic phase is dried over sodium sulphate, filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography eluting with eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) to give the title compound as a viscous oil.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washwashed successively with water and brine
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting
  8. washwith eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume)

Sources & evidence

ORD record
ord-b2c8534ea6ad4bc88ba24cd4d6bb00cd
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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