Hydrochloric Acid → HCID 20135876, compound

HRID 484896Notes

Reaction equation

HRID 484896 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([N+:19]([O-])=O)=[CH:13][C:14]=2[N+:16]([O-])=O)[C:9]([NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[N:8]1)[CH3:2].CO.O.Cl>[Fe].C(Cl)(Cl)Cl>[CH2:31]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([NH2:19])=[CH:13][C:14]=2[NH2:16])[C:9]([NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:27][CH3:28])[CH2:29][CH3:30])=[N:8]1)[CH3:32]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 20135767HCID 20135767, compound

Product 1

HCID 20135876HCID 20135876, compoundYield 23.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A mixture consisting of 12.0 g of the 1-(3-diethylaminopropyl)-3-(3-diethylaminopropylamino)-5,7-dinitroindazole, 18 g of iron powder, 60 ml of methyl alcohol, 30 ml of water and 3 ml of hydrochloric acid was stirred for 1.5 hours at 70° C. After cooling, the mixture was filtered, and the pH of the filtrate was adjusted to 11 with an aqueous potassium carbonate solution. The filtrate was extracted three times with 50 ml of ethyl acetate, and the ethyl acetate layer was washed with water. The layer was dried over anhydrous sodium sulfate, and ethyl acetate was removed under reduced pressure. The residue thus obtained was subjected to an alumina-column chromatography (alumina: 200 g) using chloroform as the developing solvent to give 2.46 g of 1-(3-diethylaminopropyl)-3-(3-diethylaminopropylamino)-5,7-diaminoindazole having the following analytical values in a yield of 23%.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. extractionThe filtrate was extracted three times with 50 ml of ethyl acetate
  4. washthe ethyl acetate layer was washed with water
  5. dry with materialThe layer was dried over anhydrous sodium sulfate, and ethyl acetate
  6. customwas removed under reduced pressure
  7. customThe residue thus obtained

Sources & evidence

ORD record
ord-b5efbfb913a5466185b4fe07023694ee
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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