Hydrochloric Acid → methyl 2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoate

HRID 2074520Notes

Reaction equation

HRID 2074520 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][O:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O.[CH3:27]O>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][O:18][C:19]([CH3:24])([CH3:23])[C:20]([O:22][CH3:27])=[O:21])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 71354Bindarit

Product 1

HCID 66846093methyl 2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoate

Procedure

A suspension of 2-[(1-benzyl-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid (20 g; 0.062 mol) in methanol (300 ml) was treated at 0° C. with gaseous HCl for 4 hours. The mixture was then poured into water (500 ml) and the product was extracted with diethyl ether (3×250 ml). The combined organic phases were washed with 5% sodium bicarbonate solution (2×100 ml) and then with water (50 ml). The solvent was evaporated off under reduced pressure and the crude residue was purified by crystallization from hexane.

Workup

  1. extractionthe product was extracted with diethyl ether (3×250 ml)
  2. washThe combined organic phases were washed with 5% sodium bicarbonate solution (2×100 ml)
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe crude residue was purified by crystallization from hexane

Sources & evidence

ORD record
ord-49faa63dfa484b418d55c0962c0149c9
Source dataset
uspto-grants-2011_04
Patent number
US07919518B2

Reaction notes

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