Methane → HCID 20159003, compound

HRID 985994Notes

Reaction equation

HRID 985994 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:13]2[C:14]([CH3:20])=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.C>>[CH3:1][C:2]1[CH:3]=[C:4]([C:13]2[C:14]([CH3:20])=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Participants

3

Reactant 2

HCID 297MethaneHCID 14221005HCID 14221005, compound

Product 1

HCID 20159003HCID 20159003, compoundYield 52.9%

Procedure

A solution of 8-methyl-6-[2,6-dimethylpyrid-3-yl]-2-(1H)-quinolone (0.30 g) was hydrogenated at 60° and 60 p.s.i. (4.13×105Pa) pressure over 10% palladised charcoal (0.10 g) for 48 hours. The cooled solution was then filtered through "Solkafloc" (Trademark for a cellulose-based filtering aid), evaporated to dryness in vacuo, and the residue chromatographed on silica (Merck "MK 60.9385") eluting with chloroform:methanol, 49:1. Combination and evaporation of appropriate fractions afforded a solid (0.16 g) which was recrystallised from ethyl acetate/methanol to give 8-methyl-6-[2,6-dimethylpyrid-3-yl]-3,4-dihydro-2-(1H)-quinoline, m.p. 255°-258° (0.110 g).

Workup

  1. customwas hydrogenated at 60°
  2. filtrationThe cooled solution was then filtered through "Solkafloc" (Trademark for a cellulose-
  3. filtrationbased filtering aid),
  4. customevaporated to dryness in vacuo
  5. customthe residue chromatographed on silica (Merck "MK 60.9385")
  6. washeluting with chloroform
  7. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-d5f169535fd04154a2f85fa2bd414d52
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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