Methane → HCID 19867069, compound

HRID 1199512Notes

Reaction equation

HRID 1199512 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=2)[NH:12][C:11](=[O:17])[CH:10]=[CH:9]3)[CH:5]=[N:4][CH:3]=[N:2]1.C>C(O)C>[CH3:16][C:14]1[CH:15]=[C:6]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=[O:17])[CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 297MethaneHCID 14450296HCID 14450296, compound

Product 1

HCID 19867069HCID 19867069, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6-(1,2,4-triazol-1-yl)-8-methyl-2-(1H)-quinolone (see Example 9) (1.7 g) in ethanol (450 cm3) was hydrogenated at 60° and 60 p.s.i. (4.13×105Pa) pressure over 10% palladised charcoal (0.35 g) for 72 hours. The cooled mixture was then filtered through "Solkafloc" (Trademark for a cellulose based filtering agent) and evaporated in vacuo to afford a solid. Chromatography on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform:methanol, 49:1, followed by combination and evaporation of the appropriate fractions in vacuo gave a solid which was recrystallised from ethyl acetate/methanol to give 3,4-dihydro-8-methyl-6-(1,2,4-triazol-1-yl)-2-(1H)-quinolone, m.p. 258°-259° (0.266 g).

Workup

  1. customwas hydrogenated at 60°
  2. filtrationThe cooled mixture was then filtered through "Solkafloc" (Trademark for a cellulose
  3. filtrationbased filtering agent) and
  4. customevaporated in vacuo
  5. customto afford a solid
  6. washChromatography on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform
  7. custommethanol, 49:1, followed by combination and evaporation of the appropriate fractions in vacuo
  8. customgave a solid which
  9. customwas recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-31cab2c20979408ab8017830b95c6ba4
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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