Diethyl Ether → HCID 13706071, compound

HRID 1730944Notes

Reaction equation

HRID 1730944 reaction equation
[CH3:1][NH:2][C:3]([CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[OH-].[Na+]>O1CCCC1>[CH3:1][NH:2][CH2:3][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 13706068N-Methyl-3-(3-phenyl-1H-indazol-1-yl)propanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 13706071HCID 13706071, compoundYield 2.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-N-Monomethylcarbamoylethyl-3-phenylindazole (m.p. 111°-112° C) (50 g) was dissolved in anhydrous tetrahydrofuran (40 ml) and to the solution was added lithium aluminum hydride (1.5 g) under cooling with ice followed by heating under reflux for 20 min. while stirring. Aqueous ether and aqueous sodium hydroxide solution were added to the resulting reaction mixture to separate an organic layer. 10% Hydrochloric acid was added to the organic layer to separate water layer. The water layer was alkalized with the addition of an aqueous sodium hydroxide solution, extracted with benzene, and the extract was washed with water, dried over sodium sulfate and concentrated under reduced pressure to obtain 1.2 g of 1-N-monomethylaminopropyl-3-phenylindazole as an oily product. The product was converted to its oxalate by a conventional way and then recrystallized from methanol to obtain crystals having a melting point between 197°-198° C (decomposition).

Workup

  1. temperatureunder cooling with ice
  2. temperatureby heating
  3. temperatureunder reflux for 20 min.
  4. customto separate an organic layer
  5. addition10% Hydrochloric acid was added to the organic layer
  6. customto separate water layer
  7. additionThe water layer was alkalized with the addition of an aqueous sodium hydroxide solution
  8. extractionextracted with benzene
  9. washthe extract was washed with water
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b748857f66204775883ea3231cf12735
Source dataset
uspto-grants-1976_11
Patent number
US03994890

Reaction notes

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