N-methyl-2-pyrrolidone → HCID 20158990, compound

HRID 985995Notes

Reaction equation

HRID 985995 reaction equation
C[S-].[Na+].Br[C:5]1[CH:6]=[C:7]([C:16]2[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[CH:8]=[C:9]2[C:14]=1NC(=O)C=C2.[CH3:24][N:25]1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30]>CO.C(Cl)(Cl)Cl.O>[CH3:29][CH:28]1[C:9]2[C:24](=[C:5]([CH3:14])[CH:6]=[C:7]([C:16]3[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[CH:8]=2)[NH:25][C:26](=[O:30])[CH2:27]1

Participants

7

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 4378561Sodium methanethiolateHCID 14221015HCID 14221015, compound

Product 1

HCID 20158990HCID 20158990, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of sodium methanethiolate (15 cm3 of a 2.0M solution in methanol) was added at room temperature to a solution of 8-bromo-6-[2,6-dimethylpyrid-3-yl]-2-(1H)-quinolone (0.50 g) and cuprous iodide (0.15 g) in N-methyl-2-pyrollidone (12 cm3). After heating at 160° for 48 hours the cooled mixture was diluted with chloroform (100 cm3) and water (50 cm3). The separated aqueous phase was further extracted with chloroform (3×50 cm3), and the combined and dried (MgSO4) chloroform extracts were evaporated in vacuo to given an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform. Combination and evaporation of appropriate fractions gave a solid which was recrystallised from ethyl acetate to afford 6-[2,6-dimethyl-pyrid-3-yl]-8-thiomethyl-2-(1H)-quinolone 0.25 H2O, m.p. 146.5°-148.5° (0.04 g).

Workup

  1. temperatureAfter heating at 160° for 48 hours the cooled mixture
  2. extractionThe separated aqueous phase was further extracted with chloroform (3×50 cm3)
  3. dry with materialdried (MgSO4) chloroform extracts
  4. customwere evaporated in vacuo
  5. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  6. washeluting with chloroform
  7. customCombination and evaporation of appropriate fractions
  8. customgave a solid which
  9. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-0d8e495a9cea404889a421630cb80fb7
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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