Potassium Carbonate → HCID 178429562, compound

HRID 2248272Notes

Reaction equation

HRID 2248272 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:19]([CH3:25])[CH2:20][C:21](=[O:24])[NH:22][N:23]=4)=[CH:17][C:11]=3[N:10]=2)C(=O)C2=CC=CC=C12.O.NN.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([C:18]3[CH:19]([CH3:25])[CH2:20][C:21](=[O:24])[NH:22][N:23]=3)=[CH:17][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 178429561HCID 178429561, compound

Product 1

HCID 178429562HCID 178429562, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25.9 g (62 mmol) of 6-[2-(3-phthalimidopropyl)-1H-benzimidazol -5-yl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 16.0 ml (330 mmol) of hydrazine hydrate are boiled under reflux in 300 ml of ethanol for 1 5 hours. The thick suspension obtained is concentrated by evaporation under vacuum and the residue is taken up with 500 ml of 2N hydrochloric acid and the solution is filtered. The filtrate is concentrated by evaporation under vacuum and after the addition of 100 ml of ethanol it is again concentrated by evaporation. The solid obtained as residue is taken up with 200 ml of saturated potassium carbonate solution and the mixture is extracted with 3×100 ml of isopropanol. The combined organic phases are dried and concentrated by evaporation under vacuum. 13·9 g (79%) of a colorless solid are obtained after recrystallization from ethanol/water.

Workup

  1. customThe thick suspension obtained
  2. concentrationis concentrated by evaporation under vacuum
  3. filtrationthe solution is filtered
  4. concentrationThe filtrate is concentrated by evaporation under vacuum
  5. additionafter the addition of 100 ml of ethanol it
  6. concentrationis again concentrated by evaporation
  7. customThe solid obtained as residue
  8. extractionthe mixture is extracted with 3×100 ml of isopropanol
  9. customThe combined organic phases are dried
  10. concentrationconcentrated by evaporation under vacuum

Sources & evidence

ORD record
ord-3d39af7d69bc49ff9fe714667233a42c
Source dataset
uspto-grants-1991_08
Patent number
US05039675

Reaction notes

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