Potassium Carbonate → HCID 12069377, compound

HRID 1368917Notes

Reaction equation

HRID 1368917 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=1)=[CH:13][C:12]([Br:27])=[CH:11][C:10]=2[CH2:28][O:29]C(=O)C)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=1)=[CH:13][C:12]([Br:27])=[CH:11][C:10]=2[CH2:28][OH:29])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 12069376HCID 12069376, compound

Product 1

HCID 12069377HCID 12069377, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.84 mmole 6-bromo-4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-8-(acetoxymethyl)quinoline-3-carboxylic acid ethyl ester (i.e., Example 14) and 1.84 mmole of potassium carbonate in 20 mL of ethanol was stirred at RT for 20 hours. The mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The resultant organic layer was dried over MgSO4 and filtered, and the filtrate concentrated to give 0.85 g of the title compound as a tan solid. MS: 481; LC: 3.43′.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe resultant organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-29c1911637a444a4b9987c74d09d18dc
Source dataset
uspto-grants-2003_06
Patent number
US06576644B2

Reaction notes

Loading…