Hydrochloric Acid → 1-(4-Methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-ylboronic acid

HRID 1696541Notes

Reaction equation

HRID 1696541 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH3:7][O:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][N:14]2[C:23]3[C:18](=[CH:19][C:20]([B:24]4[O:28]C(C)(C)C(C)(C)[O:25]4)=[CH:21][CH:22]=3)[CH:17]=[CH:16][C:15]2=[O:33])=[CH:11][CH:10]=1.Cl>C1COCC1.O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:23]3[C:18](=[CH:19][C:20]([B:24]([OH:28])[OH:25])=[CH:21][CH:22]=3)[CH:17]=[CH:16][C:15]2=[O:33])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 67271785HCID 67271785, compound

Product 1

HCID 672721411-(4-Methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-ylboronic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Sodium periodate (5.9 g, 28 mmol) was added to a solution of 1-(4-methoxybenzyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-one (3.6 g, 9.2 mmol) in THF/H2O (4/1, 40 mL). The reaction mixture was stirred at RT for 30 min, after which 2N HCl (9.2 mL) was added and the solution was then stirred at RT for 3 h. The solution was extracted with EtOAc (3×50 mL) and the organic layer was dried (MgSO4), and concentrated to yield crude 1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-ylboronic acid (2.6 g, 90% yield) which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.10 (brs, 1H), 7.96 (d, J=9.2 Hz, 1H), 7.88 (dd, J=1.6, and 8.8 Hz, 1H), 7.39 (d, J=9.2 Hz, 1H), 7.16 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 6.69 (d, J=9.6 Hz, 1H), 5.45 (brs, 2H), 3.69 (s, 3H); LC-MS (EI) m/z: 310.0 (M+H+).

Workup

  1. stirringthe solution was then stirred at RT for 3 h
  2. extractionThe solution was extracted with EtOAc (3×50 mL)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-463cb5ceb2684b7f9e13e8978f316dc9
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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