Selenium Dioxide → 3-Bromo-5-(1,3-dioxoisoindolin-2-yl)picolinaldehyde

HRID 2170359Notes

Reaction equation

HRID 2170359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:5]=[N:6][C:7]=1[CH3:8].[Se](=O)=[O:21]>COCCOC>[Br:1][C:2]1[C:7]([CH:8]=[O:21])=[N:6][CH:5]=[C:4]([N:9]2[C:10](=[O:19])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]2=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 902813522-(5-Bromo-6-methylpyridin-3-yl)isoindoline-1,3-dione

Product 1

HCID 902812293-Bromo-5-(1,3-dioxoisoindolin-2-yl)picolinaldehydeYield 383.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

To 2-(5-bromo-6-methylpyridin-3-yl)isoindoline-1,3-dione (30A, 1.5 g, 4.73 mmol) and selenium dioxide (682 mg, 6.15 mmol) was added 14 mL of DME. The reaction mixture was heated in a 130° C. heating bath for 20 hours. The reaction was repeated on identical scale 4×. The combined reaction mixtures were cooled and the solids filtered off. The filtrate was concentrated to afford 6 g of the title compound. 1H NMR (400 MHz, DMSO) δ 10.04 (s, 1H), 8.95 (d, J=1.9 Hz, 1H), 8.41 (d, J=1.7 Hz, 1H), 8.07-7.84 (m, 4H).

Workup

  1. temperatureheating bath for 20 hours
  2. customThe combined reaction mixtures
  3. temperaturewere cooled
  4. filtrationthe solids filtered off
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eeeca437af0d404ca91011d8681c51d2
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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