Hydrochloric Acid → 10-Methyl-8,9-dihydropyridazino[1',6':1,2]imidazo[4,5-c]quinoline

HRID 415539Notes

Reaction equation

HRID 415539 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][C:9]([NH:11][C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[NH:22][NH:23]C(OC(C)(C)C)=O)=[CH:19][CH:18]=[CH:17][CH:16]=3)=O)OCCO1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.Cl.[OH-].[Na+]>C(O)CCC.O>[CH3:1][C:2]1[CH2:7][CH2:8][C:9]2=[N:11][C:12]3[CH:13]=[N:14][C:15]4[C:20]([C:21]=3[N:22]2[N:23]=1)=[CH:19][CH:18]=[CH:17][CH:16]=4

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66620742Tert-butyl 2-(3-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]amino}quinolin-4-yl)hydrazinecarboxylate

Product 1

HCID 6662086810-Methyl-8,9-dihydropyridazino[1',6':1,2]imidazo[4,5-c]quinolineYield 50.6%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl 2-(3-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]amino}quinolin-4-yl)hydrazinecarboxylate (6.83 g, 16.4 mmol) and pyridinium p-toluenesulfonate (0.10 g, 0.41 mmol) in 1-butanol (125 mL) was heated to 140° C. under an atmosphere of nitrogen. After 3 h, the reaction mixture was cooled to ambient temperature, treated with HCl (38 mL, 4.3 M in ethanol) and heated (115° C.). After 1 h, the reaction mixture was concentrated under reduced pressure to give a brown solid. The solid was dissolved in water (50 mL) and treated with 50% NaOH aqueous solution until the pH of the liquid was 13. A tan solid was collected by vacuum filtration. The solid was dissolved in dichloromethane (150 mL) and washed with water (2×30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to yield 1.96 g of 10-methyl-8,9-dihydropyridazino[1′,6′:1,2]imidazo[4,5-c]quinoline as a light brown solid.

Workup

  1. temperatureheated (115° C.)
  2. waitAfter 1 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customto give a brown solid
  5. filtrationA tan solid was collected by vacuum filtration
  6. dissolutionThe solid was dissolved in dichloromethane (150 mL)
  7. washwashed with water (2×30 mL) and brine (30 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bac1baad4474d1e96b4dc00aa6257e6
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

Loading…