Sulfuric Acid → HCID 58326560, compound

HRID 2197411Notes

Reaction equation

HRID 2197411 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:15])=[CH:6][CH:7]=1.[CH:16]1(C(O)=O)[CH2:19][CH2:18][CH2:17]1.OS(O)(=O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[OH-].[NH4+]>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:15])=[CH:6][C:7]=1[CH:16]1[CH2:19][CH2:18][CH2:17]1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 19494Cyclobutanecarboxylic acidHCID 62648Ammonium PersulfateHCID 58326546HCID 58326546, compound

Product 1

HCID 58326560HCID 58326560, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent3×

Procedure

A mixture of 3-chloro-6-(2,6-dimethyl-phenyl)-pyridazine (210 mg, 0.78 mmol), cyclobutanecarboxylic acid (120 mg, 1.2 mmol), concentrated H2SO4 (300 mg) and water (3 mL) is degassed with N2 at 70° C. for 20 min. AgNO3 (34 mg, 0.2 mmol) is added followed by dropwise addition of a solution of ammonium persulfate (210 mg, 0.92 mmol) in water. The reaction mixture is stirred at the same temperature for one h. After cooled, the mixture is poured onto ice and water, neutralized with ammonium hydroxide to pH 8-9 and extracted with EtOAc. The extract is washed with water, dried and concentrated. The crude product is purified by flash silica gel column (Hexanes/EtOAc 4:1) to give 3-Chloro-4-cyclobutyl-6-(2,6-dimethyl-phenyl)-pyridazine as an oil. 1H NMR: (CDCl3) 7.26 (m, 2H), 7.14 (d, 2H), 3.78 (m, 1H), 2.48 (m, 2H), 2.00-2.20 (m, 9H), 1.90 (m, 1H).

Workup

  1. customis degassed with N2 at 70° C. for 20 min
  2. temperatureAfter cooled
  3. extractionextracted with EtOAc
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product is purified by flash silica gel column (Hexanes/EtOAc 4:1)

Sources & evidence

ORD record
ord-c4b699553ae0452db508c2309f11de6e
Source dataset
uspto-grants-2012_12
Patent number
US08338591B2

Reaction notes

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