Hydrochloric Acid → HCID 69424428, compound

HRID 350110Notes

Reaction equation

HRID 350110 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Cl)[CH:3]=1.[OH:10][C:11]1[CH:34]=[CH:33][C:14]([CH2:15][N:16]2[CH:20]=[C:19]([CH2:21][CH2:22][C:23]([O:25]C)=[O:24])[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:17]2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O.[OH-].[Li+].Cl>CO.O.O1CCCC1.CN(C)C=O>[C:27]1([C:18]2[C:19]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:20][N:16]([CH2:15][C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:8][C:4]4[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=4)=[CH:34][CH:33]=3)[N:17]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 168937Lithium hydroxide, monohydrateHCID 23024960methyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate

Product 1

HCID 69424428HCID 69424428, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-picolyl chloride hydrochloride (148 mg), methyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate (300 mg), potassium carbonate (357 mg) and N,N-dimethylformamide (5 ml) was stirred at 50° C. for 3 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatography, and a colorless oily substance was obtained from the fraction eluted with ethyl acetate. A mixture of the oily substance obtained, lithium hydroxide monohydrate (108 mg), tetrahydrofuran (6 ml), water (4 ml), and methanol (4 ml) was stirred at room temperature for 2 hours, and 1N hydrochloric acid (2.6 ml) was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The colorless crystals obtained were collected by filtration to yield 3-[3-phenyl-1-[4-(3-pyridylmethoxy)benzyl]-1H-pyrazol-4-yl]propionic acid (279 mg, yield: 78%). This was recrystallized from acetone-hexane. Melting point: 112–113° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customa colorless oily substance was obtained from the fraction
  6. washeluted with ethyl acetate
  7. additionA mixture of the oily substance
  8. customobtained
  9. extractionwas extracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated
  13. customThe colorless crystals obtained
  14. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e4ec4a31564c47a29320b3b901e5c8b8
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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