Ethyl orthoformate → HCID 68970165, compound

HRID 540849Notes

Reaction equation

HRID 540849 reaction equation
C([O:8][CH2:9][CH3:10])(OCC)OCC.C(OC)(OC)(OC)CCCC.[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]2[C:34]3[N:42]([CH3:43])[C:41]([CH3:44])=[N:40][C:35]=3[CH:36]=[N:37][C:38]=2[CH:39]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C.[Pd]>[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]2[C:34]3[N:42]([CH3:43])[C:41]([CH3:44])=[N:40][C:35]=3[CH:36]=[N:37][C:38]=2[CH:39]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1.[CH3:43][N:42]1[C:34]2[C:33]3[CH:10]=[C:9]([OH:8])[CH:30]=[CH:39][C:38]=3[N:37]=[CH:36][C:35]=2[N:40]=[C:41]1[CH3:44]

Participants

7

Reactant 3

HCID 31214Ethyl orthoformateHCID 83755Trimethyl orthovalerateHCID 68970165HCID 68970165, compound

Product 2

HCID 68970165HCID 68970165, compoundHCID 68971275HCID 68971275, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Benzyloxy-1,2-dimethyl-1H-imidazo[4,5-c]quinoline was prepared according to the methods described in Parts A-C of Example 31. In Part C, triethyl orthoformate was used in lieu of trimethyl orthovalerate. A solution of 7-benzyloxy-1,2-dimethyl-1H-imidazo[4,5-c]quinoline in ethanol was added to a Parr vessel with 10% palladium on carbon. The reaction was placed under hydrogen pressure (35 psi, 2.4×105 Pa) for 20 hours. The reaction mixture was then filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure. The residue was dissolved in acetic acid with heating, and the hot solution was filtered and concentrated under reduced pressure. The resulting beige solid was dissolved in 1 N aqueous hydrochloric acid, and deactivated carbon was added. The solution was heated, filtered, and treated with 50% aqueous sodium hydroxide. A precipitate formed and was isolated by filtration to provide 1,2-dimethyl-1H-imidazo[4,5-c]quinolin-8-ol as a solid, mp >300° C.

Workup

  1. customfor 20 hours
  2. filtrationThe reaction mixture was then filtered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in acetic acid
  6. temperaturewith heating
  7. filtrationthe hot solution was filtered
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe resulting beige solid was dissolved in 1 N aqueous hydrochloric acid
  10. additiondeactivated carbon was added
  11. temperatureThe solution was heated
  12. filtrationfiltered
  13. additiontreated with 50% aqueous sodium hydroxide
  14. customA precipitate formed
  15. customwas isolated by filtration

Sources & evidence

ORD record
ord-951358d8228c478cb014381c21bf2e61
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

Loading…