Chlorosuccinimide → HCID 59255055, compound

HRID 1809349Notes

Reaction equation

HRID 1809349 reaction equation
[CH:1]([N:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]1=[O:16])([CH3:3])[CH3:2].[Cl:17]N1C(=O)CCC1=O>CN(C)C=O>[Cl:17][C:8]1[CH:7]=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5](=[O:16])[N:4]([CH:1]([CH3:2])[CH3:3])[C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 59255053HCID 59255053, compound

Product 1

HCID 59255055HCID 59255055, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 1-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate as prepared in 1(5) (3.0 g, 13.44 mmol) and N-chlorosuccinimide (1.79 g, 13.44 mmol) in N,N-dimethylformamide (27 mL) was stirred at room temperature for 16 h, and the solvent was removed in vacuo. The residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=2/1˜1/1) to give 3.19 g (92%) of the title compound as brown oil.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=2/1˜1/1)

Sources & evidence

ORD record
ord-6b77d216a6fb4ecfb6dc5fcb170d6987
Source dataset
uspto-grants-2013_01
Patent number
US08362038B2

Reaction notes

Loading…