Chlorosuccinimide → HCID 54684290, compound

HRID 1867135Notes

Reaction equation

HRID 1867135 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[CH:3]=1.[Cl:10]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:10][C:3]1[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 546914196-Methylpyridine-2,4-diol

Product 1

HCID 54684290HCID 54684290, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

4-Hydroxy-6-methyl-1H-pyridin-2-one (25 g, 0.2 mol) and N-chlorosuccinimide (29.4 g, 0.22 mol) were dissolved in 200 mL of acetic acid. The reaction was heated at 115° C. for 6 hours. The reaction was cooled to room temperature, the solid was filtered, and washed with acetic acid and hexanes. The solid was dried in a vacuum oven overnight to give a white solid (19.2 g, 60%): 1H NMR (300 MHz, DMSO-d6) δ 11.46 (br s, 1H), 11.04 (s, 1H), 5.79 (s, 1H), 2.09 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe solid was filtered
  3. washwashed with acetic acid and hexanes
  4. customThe solid was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-681934a651f64c239b69fdee7a8b8fa1
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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