Hydrochloric Acid → HCID 20135762, compound

HRID 484868Notes

Reaction equation

HRID 484868 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:16]2[C:11](=[C:12]([N+:20]([O-])=O)[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=2)[NH:10][N:9]=1)[CH3:2].CO.O.Cl>[Fe].C(Cl)(Cl)Cl>[CH2:23]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:16]2[C:11](=[C:12]([NH2:20])[CH:13]=[C:14]([NH2:17])[CH:15]=2)[NH:10][N:9]=1)[CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 20135777N~3~-(5,7-Dinitro-1H-indazol-3-yl)-N~1~,N~1~-diethylpropane-1,3-diamine

Product 1

HCID 20135762HCID 20135762, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A mixture consisting of 9.0 g of the 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. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. Then, 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 1.67 g of 3-(3-diethylaminopropylamino)-5,7-diaminoindazole having the following analytical values in a yield of 22%.

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 materialdried over anhydrous sodium sulfate
  6. customThen, ethyl acetate was removed under reduced pressure
  7. customThe residue thus obtained

Sources & evidence

ORD record
ord-2c4e3818584b4a9499436ad7252c81e0
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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