4-Methoxyphenylacetyl chloride → HCID 178499641, compound

HRID 1471439Notes

Reaction equation

HRID 1471439 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([OH:13])=[CH:11][C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:9]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](Cl)=[O:29])=[CH:23][CH:22]=1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([OH:13])=[C:11]([C:28](=[O:29])[CH2:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:9]1

Participants

4

Reactant 2

HCID 27346884-Methoxyphenylacetyl chlorideHCID 178499531HCID 178499531, compound

Product 1

HCID 178499641HCID 178499641, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The mixture of the above obtained methyl [1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate (Compound of Formula (IV), 1 g, 3.76 mmol, 1 eq.), was suspended in dioxane (10 mL) and Ca(OH)2 (0.557 g, 2 equiv.) and (4-methoxyphenyl)acetyl chloride (0.694 g) under nitrogen, was heated at 120° C. for 45-60 minutes. The resulting red solution was concentrated in vacuo to afford a red syrup that was partitioned between ethylacetate and cold 0.1M HCl. Organic phases were washed with brine and dried over Na2SO4. Evaporation of solvent gave methyl {1-(2-chlorophenyl)-5-hydroxy-4-[(4-methoxyphenyl)acetyl]-1H-pyrazol-3-yl}acetate as a pink solid (1.09 g, 70% yield, 89% HPLC purity). MS (ESI+): 415.9; MS (ESI−): 413.8.

Workup

  1. additionThe mixture of the
  2. concentrationThe resulting red solution was concentrated in vacuo
  3. customto afford a red syrup that
  4. customwas partitioned between ethylacetate and cold 0.1M HCl
  5. washOrganic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-314415b154b74c5fb872f9a9b1c93cc5
Source dataset
uspto-grants-2015_04
Patent number
US09012449B2

Reaction notes

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