Hydrochloric Acid → 1-[5-Chloro-2-methoxy-4-methyl-3-(1H-pyrazol-4-yl)phenyl]ethanone

HRID 510905Notes

Reaction equation

HRID 510905 reaction equation
[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([C:13]2[CH:14]=[N:15][N:16](C(OCC)C)[CH:17]=2)[C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.Cl.O>O1CCCC1>[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([C:13]2[CH:17]=[N:16][NH:15][CH:14]=2)[C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 866668221-{5-Chloro-3-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-2-methoxy-4-methylphenyl}ethanone

Product 1

HCID 866668231-[5-Chloro-2-methoxy-4-methyl-3-(1H-pyrazol-4-yl)phenyl]ethanoneYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-{5-Chloro-3-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-2-methoxy-4-methylphenyl}ethanone (0.22 g, 0.65 mmol) was treated with 1.0 M hydrogen chloride in water (3.9 mL, 3.9 mmol) in tetrahydrofuran (4 mL) overnight. The mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layers were dried over MgSO4, filtered, concentrated and purified on silica gel (eluting with 0-60% of ethyl acetate in hexane) to afford the desired product (0.13 g, 75%). LCMS calculated for C13H14ClN2O2 (M+H)+: m/z=265.1. found: 265.0.

Workup

  1. customThe mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel (eluting with 0-60% of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b801acb313b94186a801e6fd9b766b17
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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