Carbon Dioxide → HCID 135583105, compound

HRID 484890Notes

Reaction equation

HRID 484890 reaction equation
[Mg].[CH2:2]([N:4]([CH2:27][CH3:28])[CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[C:12](Cl)[CH:13]=[CH:14][CH:15]=2)[C:10]([NH:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[N:9]1)[CH3:3].C(Br)(C)C.O=O.C(=O)=[O:36].S(=O)(=O)(O)O>O.C(OCC)C>[CH2:2]([N:4]([CH2:27][CH3:28])[CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[C:12]([OH:36])[CH:13]=[CH:14][CH:15]=2)[C:10]([NH:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[N:9]1)[CH3:3]

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 977OxygenHCID 1118Sulfuric AcidHCID 63582-BromopropaneHCID 5462224MagnesiumHCID 20135776HCID 20135776, compound

Product 1

HCID 135583105HCID 135583105, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To 20 ml of diethyl ether containing 600 mg of magnesium powder was added dropwise a mixed solution consisting of 3.92 g of the 1-(3-diethylaminopropyl)-3-(3-diethylaminopropylamino)-4-chloroindazole, 2.06 g of isopropyl bromide and 20 ml of diethyl ether. Into the mixed solution were introduced dried oxygen gas and dried carbon dioxide gas for 12 hours so as to reflux the solution, and the solution was left to stand for 12 hours. The pH of the solution was adjusted to 4.0 by adding dropwise sulfuric acid to the solution at 0° C. The solution was added with 50 ml of water and filtered. To the aqueous layer of the filtrate was added an aqueous potassium carbonate solution to separate crystals. The crystals were obtained by filtration and dried to give 1.46 g of 1-(3-diethylaminopropyl)-3-(3-diethylaminopropylamino)-4-hydroxyindazole having the following analytical values in a yield of 39%.

Workup

  1. temperatureto reflux the solution
  2. waitthe solution was left
  3. filtrationfiltered
  4. additionTo the aqueous layer of the filtrate was added an aqueous potassium carbonate solution
  5. customto separate crystals
  6. customThe crystals were obtained by filtration
  7. customdried

Sources & evidence

ORD record
ord-5e462ba6c2a445b38ce7e09d39416e82
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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