Acetic Acid → HCID 69281520, compound

HRID 1487665Notes

Reaction equation

HRID 1487665 reaction equation
[Cl:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[N+:13]([O-])=O.C(O)(=O)C>O.[Fe]>[Cl:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[N:5]=[CH:4][C:3]=1[NH2:13]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69093111HCID 69093111, compound

Product 1

HCID 69281520HCID 69281520, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 5-chloro-4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole (1 equiv) and iron dust (3 equiv) in water (0.35 M) was added acetic acid (3.54 M). The mixture was heated to 90° C. for 1.5 h then cooled to room temperature. The reaction was quenched by addition of solid sodium bicarbonate and treated with ethyl acetate (0.06M) with continuous stirring. The mixture was filtered and the filter cake was rinsed with ethyl acetate. The combined filtrate was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (1.5% MeOH in DCM) to provide the desired product (52% yield) as a brown oil. MS (ESI) m/z 202.1 [M+H]+.

Workup

  1. temperaturethen cooled to room temperature
  2. customThe reaction was quenched by addition of solid sodium bicarbonate
  3. additiontreated with ethyl acetate (0.06M) with continuous stirring
  4. filtrationThe mixture was filtered
  5. washthe filter cake was rinsed with ethyl acetate
  6. dry with materialThe combined filtrate was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel chromatography (1.5% MeOH in DCM)

Sources & evidence

ORD record
ord-9191dd3a8f354ceaa70e8e0e9041a126
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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