Benzoyl chloride → HCID 44219523, compound

HRID 76116Notes

Reaction equation

HRID 76116 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][O:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])=[N:2]1.C([O-])([O-])=O.[K+].[K+].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+]>CC(C)=O.O>[C:24]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][O:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])=[N:2]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 178459030HCID 178459030, compound

Product 1

HCID 44219523HCID 44219523, compoundYield 22.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2-(1H-indazol-3-ylmethoxy)-2-methylpropanoic acid (6 g; 0.026 mol) in acetone (50 ml) stirred at room temperature was added K2CO3 (6.8 g; 0.049 mol) and then, slowly, a solution of benzoyl chloride (5 ml; 0.043 mol) in acetone (30 ml). The mixture was stirred at room temperature for 24 hours and then poured into water (1 L). The solution was then brought to basic pH with 5N NaOH and washed with diethyl ether (3×150 ml). The alkaline phase was then acidified with concentrated HCl and extracted with diethyl ether (3×300 ml). The combined organic phases were concentrated under reduced pressure and the crude residue obtained was purified by crystallization from a 1/1 hexane/ethyl acetate mixture. 2 g of 2-[(1-benzoyl-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid were obtained, m.p.=132-135° C.

Workup

  1. washwashed with diethyl ether (3×150 ml)
  2. extractionextracted with diethyl ether (3×300 ml)
  3. concentrationThe combined organic phases were concentrated under reduced pressure
  4. customthe crude residue obtained
  5. customwas purified by crystallization from a 1/1 hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-66d08c1482514ff997c4bd7988b314be
Source dataset
uspto-grants-2014_09
Patent number
US08835481B2

Reaction notes

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