Ethyl Acetate → 5-Methoxy-6-nitropicolinic acid

HRID 509390Notes

Reaction equation

HRID 509390 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[N:5]C(C)=[CH:7][CH:8]=1.[O-][Mn](=O)(=O)=O.[K+].CC[O:21][C:22]([CH3:24])=[O:23]>O.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:24]([C:22]([OH:21])=[O:23])=[N:5][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516875Potassium PermanganateHCID 27279653-Methoxy-6-methyl-2-nitropyridine

Product 1

HCID 225980405-Methoxy-6-nitropicolinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 3-methoxy-6-methyl-2-nitropyridine (7 g, 0.041 mol) in water (140.0 mL) was added KMnO4 (32.88 g, 0.208 mol, S.d. fine chemicals, India) at 80° C. The reaction mixture was stirred for 16 h at 100° C. After completion of the reaction (monitored by TLC, 50% EtOAc in hexane), the reaction mixture was filtered and the solids were washed with water. The filtrate was acidified and extracted with EtOAc (500 mL×2). The organic layers were then dried over sodium sulfate and concentrated under reduced pressure to afford the title compound as an off white solid. 1H-NMR (400 MHz, DMSO-d6): δ 13.6 (br. s., 1H), 8.39 (d, J=8.8 Hz, 1H), 8.09 (d, J=8.8 Hz, 1H), 4.06 (s, 3H). MS (ESI, positive ion) m/z: 199 (M+H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe solids were washed with water
  3. extractionextracted with EtOAc (500 mL×2)
  4. dry with materialThe organic layers were then dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26a201f8853f475193aeedfbfe0bb829
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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