4-Fluorophenylhydrazine hydrochloride → HCID 67199165, compound

HRID 1423016Notes

Reaction equation

HRID 1423016 reaction equation
[CH2:1]([O:3][C:4](=[O:19])/[C:5](=[CH:15]\[N:16](C)C)/[C:6](=O)[CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[CH3:2].Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28]N)=[CH:24][CH:23]=1>CO>[CH2:1]([O:3][C:4]([C:5]1[CH:15]=[N:16][N:28]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)[C:6]=1[CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[O:19])[CH3:2]

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 873054892102885-50-5

Product 1

HCID 67199165HCID 67199165, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[1-dimethylamino-meth-(Z)-ylidene]-4,4-diethoxy-3-oxo-butyric acid ethyl ester (625 mg, 2.28 mmol) in methanol (10 mL) is added 4-fluorophenylhydrazine hydrochloride (410 mg, 2.5 mmol). The mixture is warmed at reflux. After 2 hours, the reaction mixture is cooled to room temperature, concentrated in vacuo, diluted with water (15 mL) and extracted with ether (3×15 mL). The combined ether layers are washed with brine (2×15 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0-10% EtOAc in hexanes to afford 5-diethoxymethyl-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester.

Workup

  1. temperatureThe mixture is warmed
  2. temperatureat reflux
  3. concentrationconcentrated in vacuo
  4. additiondiluted with water (15 mL)
  5. extractionextracted with ether (3×15 mL)
  6. washThe combined ether layers are washed with brine (2×15 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified by silica gel chromatography
  11. washeluting with a gradient of 0-10% EtOAc in hexanes

Sources & evidence

ORD record
ord-316d20afa753494fabec87e42dab85c6
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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