Acetic Acid → HCID 67776453, compound

HRID 2202415Notes

Reaction equation

HRID 2202415 reaction equation
[Cl:1][C:2]1[C:3](=[O:30])[N:4]([C:19]2[C:24]([CH3:25])=[CH:23][N:22]=[C:21]([C:26]([O:28]C)=[O:27])[CH:20]=2)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[OH-].[Na+].C(O)(=O)C>O1CCOCC1>[Cl:1][C:2]1[C:3](=[O:30])[N:4]([C:19]2[C:24]([CH3:25])=[CH:23][N:22]=[C:21]([C:26]([OH:28])=[O:27])[CH:20]=2)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67777821HCID 67777821, compound

Product 1

HCID 67776453HCID 67776453, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3-chloro-4-[(2,4-difluorobenzyl)oxy]-5′,6-dimethyl-2-oxo-2H-1,4′-bipyridine-2′-carboxylate (0.13 g, 0.3 mmol) and 1.5 N NaOH (0.25 mL, 0.375 mmol) in dioxane (0.25 mL) was heated at 60° C. for 1 h and stirred at room temperature for an additional hr. The reaction mixture was acidified with acetic acid, and extracted with ethyl acetate (2×15 mL). The combined organic extract were washed with water and concentrated under reduced pressure to give the title compound as a white powder (0.08 g) which was used without purification in the next step. ES-MS, m/z=421 (M+H).

Workup

  1. extractionextracted with ethyl acetate (2×15 mL)
  2. extractionThe combined organic extract
  3. washwere washed with water
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-986b1e6567ee419db58176c6c7eaec36
Source dataset
uspto-grants-2016_06
Patent number
US09365546B2

Reaction notes

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