Water → HCID 66886106, compound

HRID 1043445Notes

Reaction equation

HRID 1043445 reaction equation
[F:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[N+:17]([O-:19])=[O:18])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)(O)[O-:21].[Na+].S([O-])([O-])(=O)=O.[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+].N([O-])=O.[Na+].OS(O)(=O)=O.[OH2:46]>O=[Mn]=O.CC(C)=O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:9](=[O:21])[C:8]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:46])=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

10

Reactant 7

HCID 962WaterHCID 1118Sulfuric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium Permanganate2×HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 668866782-Fluoro-3-[2-(4-fluoro-2-nitrophenyl)ethynyl]pyridine

Product 1

HCID 66886106HCID 66886106, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent

Procedure

A 250 mL Erlenmeyer flask, immersed in a water bath at 25° C., was charged with acetone (20 mL) and 2-fluoro-3-[(4-fluoro-2-nitrophenyl)ethynyl]pyridine (0.443 g, 0.0017 mol). To this solution was added a solution of sodium bicarbonate (0.08 g, 0.001 mol) and magnesium sulfate (0.4 g, 0.003 mol) in water (10 mL). The mixture was stirred with a mechanical stirrer. Powdered potassium permanganate (0.91 g, 0.0058 mol) was then added in one portion, and the mixture was stirred for 4 hours. The unreacted potassium permanganate and the precipitated MnO2 were reduced to soluble Mn2+ ions by adding a minimum quantity of NaNO2 (0.14 g) and 10% H2SO4 (1.4 mL) in small portions. The solution was transferred to a 250 mL separating funnel, saturated with NaCl, and extracted with ethyl acetate 2×, dried over MgSO4, concentrated and was purified by column chromatography on silica gel. (20% ethyl acetate, 80% hexanes) to give 0.45 g of the desired product. 1H NMR (400 MHz, CDCl3): δ 8.51-8.53 (m, 1H), 8.41-8.46 (m, 1H), 7.88-7.95 (m, 2H), 7.58-7.62 (m, 1H), 7.41-7.45 (m, 1H). MS [M+H]=292.9.

Workup

  1. customA 250 mL Erlenmeyer flask, immersed in a water bath at 25° C.
  2. stirringthe mixture was stirred for 4 hours
  3. customseparating funnel
  4. extractionsaturated with NaCl, and extracted with ethyl acetate 2×
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f0a0ccea7fb14683bc46e47595ff4b5d
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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