Hydrazine hydrate (1:1) → HCID 178429560, compound

HRID 1032257Notes

Reaction equation

HRID 1032257 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[NH:14][C:13]3[CH:15]=[CH:16][C:17]([C:19]4[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=4)=[CH:18][C:12]=3[N:11]=2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([C:19]3[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=3)=[CH:18][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178429559HCID 178429559, compound

Product 1

HCID 178429560HCID 178429560, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

##STR69## 0.54 g (1.26 mmol) of 6-[2-(4-phthalimidobutyl)-1H-benzimidazol-5-yl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 0.3 ml (6.3 mmol) of hydrazine hydrate are boiled in 20 ml of ethanol for 2 hours. After cooling to room temperature, the solution is filtered, the filtrate is concentrated by evaporation under vacuum and the residue is taken up with 10 ml of 2N hydrochloric acid. The resulting solution is again filtered and is then adjusted to pH 11 with 3N sodium hydroxide solution and concentrated by evaporation to half its original volume. On cooling in an ice bath, a colourless solid crystallizes, which is recrystallized from ethanol. 0.26 g (69%) of crystals are obtained which melt at 185° to 187° C. and resolidify but thereafter do not melt until heated to 280° C.

Workup

  1. filtrationthe solution is filtered
  2. concentrationthe filtrate is concentrated by evaporation under vacuum
  3. filtrationThe resulting solution is again filtered
  4. concentrationconcentrated by evaporation to half its original volume
  5. temperatureOn cooling in an ice bath
  6. customa colourless solid crystallizes
  7. customwhich is recrystallized from ethanol

Sources & evidence

ORD record
ord-1eddc9e836954a8e9ee92de8a0b8225d
Source dataset
uspto-grants-1990_09
Patent number
US04957920

Reaction notes

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