Dichloroacetic Acid → HCID 67777821, compound

HRID 2202414Notes

Reaction equation

HRID 2202414 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=2)[C:8](=[O:24])[CH:7]=1.[Cl:30]N1C(=O)CCC1=O.ClC(Cl)C(O)=O>CC(O)C>[Cl:30][C:7]1[C:8](=[O:24])[N:9]([C:13]2[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=2)[C:10]([CH3:12])=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6597Dichloroacetic AcidHCID 31398ChlorosuccinimideHCID 67777494HCID 67777494, compound

Product 1

HCID 67777821HCID 67777821, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-[(2,4-difluorobenzyl)oxy]-5′,6-dimethyl-2-oxo-2H-1,4′-bipyridine-2′-carboxylate (0.15 g, 0.375 mmol), N-chlorosuccinimide (0.06 g, 0.43 mmol) in 2-propanol (3.0 mL) containing dichloroacetic acid (0.05 mL) was heated at 60° C. under nitrogen for 2 h. The reaction mixture was concentrated, and the residue was purified by silica-gel flash chromatography using 4% methanol in ethyl acetate. Appropriate fractions were combined and concentrated under reduced pressure to give 0.15 g of the title compound. ES-MS, m/z=435 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica-gel flash chromatography
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d0effe0f3264da9911da71e71570a49
Source dataset
uspto-grants-2016_06
Patent number
US09365546B2

Reaction notes

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