Water → HCID 12582765, compound

HRID 1075899Notes

Reaction equation

HRID 1075899 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)/C=C\C(O)=O.[Cl:18][C:19]1[N:24]=[N:23][C:22]2[CH2:25][CH2:26][NH:27][CH2:28][C:21]=2[CH:20]=1.C(N(CC)CC)C.O>C(Cl)CCl>[C:1]([N:27]1[CH2:26][CH2:25][C:22]2[N:23]=[N:24][C:19]([Cl:18])=[CH:20][C:21]=2[CH2:28]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86733381HCID 86733381, compound

Product 1

HCID 12582765HCID 12582765, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of 12.6 g of benzoyl chloride in 100 cc of ethylene chloride is added dropwise to a suspension of 25.6 g of 3-chloro-5,6,7,8-tetrahydropyrido [4,3-c]pyridazine maleate in 250 cc of ethylene chloride and 21.8 g of triethylamine within 18 minutes at room temperature while stirring. The mixture is stirred at room temperature for a further 14 hours, 200 cc of water are added, the organic phase is separated and concentrated to an oil in a vacuum. Upon adding ether/dimethoxyethane to this oil, crude 6-benzoyl-3-chloro-5,6,7,8-tetrahydropyrido[4,3-c]pyridazine is obtained. After recrystallization from absolute ethanol with the addition of a small amount of coal, the compound has a M.P. of 125°-127° (decomp.).

Workup

  1. stirringThe mixture is stirred at room temperature for a further 14 hours
  2. customthe organic phase is separated
  3. concentrationconcentrated to an oil in a vacuum
  4. additionUpon adding ether/dimethoxyethane to this oil

Sources & evidence

ORD record
ord-99cb6240385e464ba781f084351fa2f1
Source dataset
uspto-grants-1976_05
Patent number
US03954754

Reaction notes

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