Sodium hydride → HCID 68139543, compound

HRID 1730934Notes

Reaction equation

HRID 1730934 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[CH:14]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:19]([N:21]([CH2:24][CH2:25][CH2:26][Cl:27])[CH2:22][CH3:23])[CH3:20]>CN(C)C=O.C1(C)C=CC=CC=1>[ClH:27].[CH2:19]([N:21]([CH2:22][CH3:23])[CH:24]([C:14]1[C:13]([CH3:16])=[CH:12][CH:11]=[C:10]2[C:15]=1[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[N:8][NH:9]2)[CH2:25][CH3:26])[CH3:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 669183-Chloropropyl(diethyl)amineHCID 6104125-Methyl-3-phenyl-1H-indazole

Product 1

HCID 68139543HCID 68139543, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

3-Phenyl-5-methylindazole (4.17 g) was dissolved in dimethylformamide (70 ml) and sodium hydride 50% pure (1.15 g) was added to the solution, followed by stirring it at room temperature for 10 min. To the resulting solution was added dropwise a solution of diethylaminopropyl chloride (3.59 g) in 30 ml of toluene. The mixture was stirred at 70° C for 1 hour and poured into ice-water, and extracted with chloroform. The extract was washed with water, dried over sodium sulfate and concentrated by evaporation. The residue was treated with ether-hydrochloric acid to obtain 4.5 g of 1-diethylaminopropyl-3-phenyl-5-methylindazole hydrochloride (m.p. 127°-129° C).

Workup

  1. stirringThe mixture was stirred at 70° C for 1 hour
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation
  6. additionThe residue was treated with ether-hydrochloric acid

Sources & evidence

ORD record
ord-ca8c00332bf1402b8f00cf453d88ced6
Source dataset
uspto-grants-1976_11
Patent number
US03994890

Reaction notes

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