Sodium Carbonate → HCID 71294337, compound

HRID 240691Notes

Reaction equation

HRID 240691 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=2)[CH:10]=1)=O.O.[NH2:26][NH2:27].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:10]=[C:5]([C:3]([NH:26][NH2:27])=[O:2])[CH:6]=[N:7][C:8]=2[O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:12][C:13]=1[F:18]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 71293979HCID 71293979, compound

Product 1

HCID 71294337HCID 71294337, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

5-(4-Chloro-3-fluoro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-3-pyridinecarboxylic acid methyl ester (97 mg, 267 μmol) was dissolved in ethanol (2 mL) to give a light yellow solution. Hydrazine monohydrate (134 mg, 130 μl, 2.67 mmol) was added under argon. The reaction mixture was stirred under argon at reflux temperature (85° C.) for 5 h. Subsequently the reaction mixture was poured into 10 mL saturated aqueous Na2CO3 solution and extracted with isopropyl acetate (2×20 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo to give the title compound (63 mg, 65%) as off-white solid; MS (ESI) 361.8 (M−H)−.

Workup

  1. customto give a light yellow solution
  2. extractionextracted with isopropyl acetate (2×20 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4594e1fe6da8447f8c3e08cd3cb5565d
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

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