2,5-Dihydroxybenzoic acid → HCID 12582680, compound

HRID 1075907Notes

Reaction equation

HRID 1075907 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]2[CH2:8][CH2:9][N:10]([C:12](=[O:21])[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=3[CH3:20])[CH2:11][C:4]=2[CH:3]=1.O.[NH2:23][NH2:24].C1C(O)=CC(C(O)=O)=C(O)C=1>O1CCOCC1>[CH3:20][C:14]1[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]([N:10]1[CH2:9][CH2:8][C:5]2[N:6]=[N:7][C:2]([NH:23][NH2:24])=[CH:3][C:4]=2[CH2:11]1)=[O:21]

Participants

5

Reactant 3

HCID 34692,5-Dihydroxybenzoic acidHCID 24654Hydrazine hydrate (1:1)HCID 20441591HCID 20441591, compound

Product 1

HCID 12582680HCID 12582680, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10.3 g of 3-chloro-6-(2,3-dimethylbenzoyl)-5,6,7,8-tetrahydropyrido[4,3-c]pyridazine and 50 cc of hydrazine hydrate in 80 cc of dioxane are heated in an oil bath of 80°. After a reaction time of 60 hours, the mixture is concentrated in a vacuum, the oily residue is divided between 250 cc of chloroform and 150 cc of water, and after concentrating the chloroform phase, the resulting oily crude base is reacted with gentisic acid as described in Example 10. The gentisinate of the title compound has a M.P. of 176°-179° (decomp.) after recrystallization from 150 cc of methanol and 100 cc of water.

Workup

  1. concentrationAfter a reaction time of 60 hours, the mixture is concentrated in a vacuum
  2. concentrationafter concentrating the chloroform phase
  3. customthe resulting oily crude base is reacted with gentisic acid

Sources & evidence

ORD record
ord-7eef489bab3f4e819e58b47c626f4d13
Source dataset
uspto-grants-1976_05
Patent number
US03954754

Reaction notes

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