Oxalic Acid → HCID 59226538, compound

HRID 1523504Notes

Reaction equation

HRID 1523504 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]([O:20][CH3:21])=[O:19])=[N:6][C:7]=1[CH:8]1[CH2:17][CH2:16][C:11]2(OCC[O:12]2)[CH2:10][CH2:9]1.C(O)(=O)C(O)=O.C([O-])(O)=O.[Na+].C(OCC)(=O)C>CC(C)=O.O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]([O:20][CH3:21])=[O:19])=[N:6][C:7]=1[CH:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]1

Participants

8

Reactant 4

HCID 971Oxalic AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59226427HCID 59226427, compound

Product 1

HCID 59226538HCID 59226538, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl 5-fluoro-6-(1,4-dioxaspiro[4.5]decan-8-yl)picolinat (1.0 equiv.) in acetone and water (1:1, 0.04 M) was added oxalic acid dehydrate (2.0 equiv.) and the reaction mixture was stirred for 3 days. The solution was then neutralized by the addition of solid NaHCO3, the mixture was added to ethyl acetate and brine, the organic phase was dried over magnesium sulfate, filtered, and concentrated. Methyl 5-fluoro-6-(4-oxocyclohexyl)picolinate was obtained in 98% yield. LC/MS=252.1 (M+H), Rt=0.68 min.

Workup

  1. dry with materialthe organic phase was dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-15b1ed1c97804f7c8f031ec80cada326
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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