Chlorosuccinimide → HCID 54724229, compound

HRID 1867037Notes

Reaction equation

HRID 1867037 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:4](=[O:16])[CH:3]=1.C1C(=O)N([Cl:24])C(=O)C1>C(Cl)Cl>[Cl:24][C:3]1[C:4](=[O:16])[N:5]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:6]([CH3:8])=[CH:7][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 54679301HCID 54679301, compound

Product 1

HCID 54724229HCID 54724229, compoundYield 224.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-hydroxy-6-methyl-1-(pyridin-3-ylmethyl)pyridin-2(1H)-one (1.016 g, 4.7 mmol) in MeCl2 (10 mL) was added NCS (1.21 g, 1.78 mmol). The reaction mixture stirred at room temperature for 24 hours under nitrogen. The suspension was chilled in an ice bath and filtered. The solid was washed with fresh MeCl2 and dried to afford a yellow solid (1.00 g, 85%) after drying. 1H-NMR (CD3OD, 400 MHz) δ 8.54 (m, 2H), 7.85 (d, 1H, J=1.6 Hz), 7.61 (m, 1H), 6.10 (s, 1H), 5.41 (s, 2H), 2.33 (s, 3H); ES-LRMS (M+H) m/z 251/253.

Workup

  1. temperatureThe suspension was chilled in an ice bath
  2. filtrationfiltered
  3. washThe solid was washed with fresh MeCl2
  4. customdried

Sources & evidence

ORD record
ord-adf60a3152cb40f1b3ef243d8a2b6a85
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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