Potassium Carbonate → HCID 12763962, compound

HRID 616705Notes

Reaction equation

HRID 616705 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]2[CH:20]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:1]=[C:2]2[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66144Ethyl bromopyruvateHCID 140674074-Chloroquinolin-2-amine

Product 1

HCID 12763962HCID 12763962, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 200 ml. of N,N-dimethylformamide is added 17.9 g. (0.10 mole) of 2-amino-4-chloroquinoline and 15.2 g. (0.11 mole) potassium carbonate. To this stirred slurry is added dropwise over 20 minutes 21.5 g. (0.11 mole) of ethyl bromopyruvate and the resulting mixture stirred for two hours. The solvent is then removed in vacuo and the residue was triturated with water, extracted three times with ethyl acetate, the extracts dried over anhydrous sodium sulfate, carbon treated, filtered and the solvent evaporated to afford the title compound. Further purification is achieved by crystallization or silica gel chromatography.

Workup

  1. additionTo this stirred slurry is added dropwise over 20 minutes 21.5 g
  2. customThe solvent is then removed in vacuo
  3. customthe residue was triturated with water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialthe extracts dried over anhydrous sodium sulfate, carbon
  6. additiontreated
  7. filtrationfiltered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-88cc3fadfea24e24b29f90dc3851a99b
Source dataset
uspto-grants-1978_02
Patent number
US04075343

Reaction notes

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