Chloroform → HCID 67801881, compound

HRID 1900805Notes

Reaction equation

HRID 1900805 reaction equation
[N:1]([CH2:4][CH:5]([CH:7]1[O:21][C:10]2=[C:11]3[C:16](=[C:17]([CH3:19])[CH:18]=[C:9]2[CH2:8]1)[NH:15][C:14](=[O:20])[CH:13]=[CH:12]3)[OH:6])=[N+]=[N-].[H][H].C(Cl)(Cl)[Cl:25]>O1CCCC1.CO.Cl.O1CCOCC1.[Pd]>[NH2:1][CH2:4][CH:5]([CH:7]1[O:21][C:10]2=[C:11]3[C:16](=[C:17]([CH3:19])[CH:18]=[C:9]2[CH2:8]1)[NH:15][C:14](=[O:20])[CH:13]=[CH:12]3)[OH:6].[ClH:25]

Participants

8

Reactant 3

HCID 6212ChloroformHCID 23369753HCID 23369753, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67801881HCID 67801881, compoundYield 71.6%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

2-(2-Azido-1-hydroxyethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.01 g, 3.53 mmol) was dissolved in tetrahydrofuran (100 ml), to which 10% palladium-on-carbon (1.01 g) was added for hydrogen replacement and stirred at room temperature for 3 hours. The reaction mixture was filtered, and the filtrate was condensed under reduced pressure. The residue was dissolved in a solvent mixture of methanol (40 ml) and chloroform (10 ml), to which 4N-HCl-dioxane (0.94 ml) was added while cooling in a water bath, followed by condensing under reduced pressure. The resultant residue was recrystallized from methanol-ether to obtain 749 mg of the title compound as pale yellow powdery crystals (71.6%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed under reduced pressure
  3. additionwas added
  4. temperaturewhile cooling in a water bath
  5. customfollowed by condensing under reduced pressure
  6. customThe resultant residue was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-1f004b9ccd644286abf6dc7b7d620e0e
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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