Hydrochloric Acid → HCID 20135816, compound

HRID 484850Notes

Reaction equation

HRID 484850 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[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]([NH2:22])=[N:8]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][N:7]1[C:15]2[C:10](=[CH:11][C:12]([NH2:19])=[CH:13][C:14]=2[NH2:16])[C:9]([NH2:22])=[N:8]1)[CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 20135766HCID 20135766, compound

Product 1

HCID 20135816HCID 20135816, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A mixture consisting of 9.0 g of 1-(3-diethylaminopropyl)-3-amino-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 the reaction mixture was cooled, the mixture was filtered. The pH of the filtrate was adjusted to 11 with an aqueous potassium carbonate solution and 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, 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 1.78 g of 1-(3-diethylaminopropyl)-3,5,7-triaminoindazole having the following analytical values in a yield of 23%.

Workup

  1. temperatureAfter the reaction mixture was cooled
  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, and ethyl acetate
  6. customwas removed under reduced pressure
  7. customThe residue thus obtained

Sources & evidence

ORD record
ord-72fed2bb54a24bd686603c0ad7e9a239
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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