Dimethylformamide → 1-(3-Diethylaminopropyl)-3-phthalimido-4-chloroindazole

HRID 580147Notes

Reaction equation

HRID 580147 reaction equation
CN(C)C=O.[C:6]1(=[O:26])[N:10]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[Cl:20])[NH:13][N:12]=2)[C:9](=[O:21])[C:8]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:7]12.Br.Br[CH2:29][CH2:30][CH2:31][N:32]([CH2:35][CH3:36])[CH2:33][CH3:34].[K]>O>[CH2:33]([N:32]([CH2:35][CH3:36])[CH2:31][CH2:30][CH2:29][N:13]1[C:14]2[C:19](=[C:18]([Cl:20])[CH:17]=[CH:16][CH:15]=2)[C:11]([N:10]2[C:9](=[O:21])[C:8]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:7]3[C:6]2=[O:26])=[N:12]1)[CH3:34]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 5462222PotassiumHCID 12639158(3-Bromopropyl)diethylamine hydrobromideHCID 132297712-(4-chloro-1H-indazol-3-yl)isoindoline-1,3-dione

Product 1

HCID 132297721-(3-Diethylaminopropyl)-3-phthalimido-4-chloroindazoleYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 60 ml of anhydrous N,N-dimethylformamide were added 4.54 g of 3-phthalimido-4-chloroindazole obtained in the same method as described in Example 1, 4.83 g of 3-bromopropyldiethylamine hydrobromide and 6.3 g of anhydrous potassium for 12 hours at 80° C. After cooling, the mixture was added with 80 ml of water and extracted with diethyl ether. The diethyl ether layer was extracted three times with 2N hydrochloric acid, and the hydrochloric acid layer was washed with diethyl ether. After the pH of the layer was adjusted to 14 with potassium carbonate, the layer was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and chloroform was removed under reduced pressure to give 3.70 g of 1-(3-diethylaminopropyl)-3-phthalimido-4-chloroindazole having the following analytical values in a yield of 59 %.

Workup

  1. customobtained in the same method
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. extractionThe diethyl ether layer was extracted three times with 2N hydrochloric acid
  5. washthe hydrochloric acid layer was washed with diethyl ether
  6. extractionthe layer was extracted with chloroform
  7. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate and chloroform
  8. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-7a948717b77d4f9c9171a3f1b49dcd45
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

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