Ethanol → HCID 66727284, compound

HRID 1361174Notes

Reaction equation

HRID 1361174 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=1.[OH-].[Na+].[CH2:19](O)C>>[CH3:15][S:12]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][CH3:19])[N:7]=1)[C:3]([OH:2])=[O:16])(=[O:14])=[O:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 59278507HCID 59278507, compound

Product 1

HCID 66727284HCID 66727284, compound

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methanesulfonyl-6-methoxy-isonicotinic acid methyl ester (4.3 g, 17.5 mmol) in ethanol (75 mL) was added 2 N aqueous sodium hydroxide (35 mL, 70 mmol). The mixture was warmed at 80° C. for 4 hours and then concentrated in vacuo to remove the ethanol. The remaining aqueous solution was acidified with 1 N aqueous HCl and extracted with ethyl acetate (4×30 mL). The combined organic layers were washed with brine (2×100 mL), dried over sodium sulfate and concentrated to afford 2-methanesulfonyl-6-ethoxy-isonicotinic acid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the ethanol
  3. extractionextracted with ethyl acetate (4×30 mL)
  4. washThe combined organic layers were washed with brine (2×100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e99780d113d2491aaba137aca8e1fdd2
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

Loading…