Hydrochloric Acid → (2-Methyl-1-oxoisoindolin-5-yl)boronic acid

HRID 216976Notes

Reaction equation

HRID 216976 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:11]3[O:15]C(C)(C)C(C)(C)[O:12]3)[CH:8]=2)[C:3]1=[O:20].Cl>CC(C)=O>[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:11]([OH:15])[OH:12])[CH:8]=2)[C:3]1=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 576912242-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Product 1

HCID 59568610(2-Methyl-1-oxoisoindolin-5-yl)boronic acidYield 72.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of crude 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (Example 31, step (ii), 53 g) in acetone (600 mL) was added aqueous HCl solution (2M, 600 mL) and the solution was heated at reflux for 18 h. The solution was concentrated under vacuum to remove acetone and then cooled to 10° C. The resulting precipitate was filtered and dried under vacuum to afford the sub-titled compound (26.8 g).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 18 h
  3. concentrationThe solution was concentrated under vacuum
  4. customto remove acetone
  5. filtrationThe resulting precipitate was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2f1377215d7c4365b61015460ad41b0e
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

Loading…