Sodium ethoxide → HCID 58585859, compound

HRID 1297734Notes

Reaction equation

HRID 1297734 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:9]2Cl)=[O:5])[CH3:2].[O-:21][CH2:22][CH3:23].[Na+]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:9]2[O:21][CH2:22][CH3:23])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 58585853HCID 58585853, compound

Product 1

HCID 58585859HCID 58585859, compound

Procedure

4-Chloro-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester (example 61f, 7.96 g, 25.4 mmol) was dissolved in anhydrous alcohol (500 mL) which containing sodium ethoxide (3.45 g, 50.8 mmol). The mixture was heated at 60 degrees for 6 hours under stirring. After the reaction, the solvent was evaporated under reduced pressure, and then dichloromethane was added. After filtration, the filtrate was concentrated to give 4-ethoxy-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester, which was used for next step without further purification. LC-MS m/e 324 (MH+).

Workup

  1. temperatureThe mixture was heated at 60 degrees for 6 hours
  2. customAfter the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. additiondichloromethane was added
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4a3aca98187344d082b7efefc375ec2f
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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