Styrene → HCID 86675937, compound

HRID 572689Notes

Reaction equation

HRID 572689 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[N:11][OH:12])[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:13][CH:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][N:11]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 7501StyreneHCID 23665760Sodium HypochloriteHCID 136413234HCID 136413234, compound

Product 1

HCID 86675937HCID 86675937, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold mixture of 6-chloro-2-methyl-3-oxo-2,3-dihydropyridazine-4-carbaldehyde oxime (300 mg, 1.599 mmol, Preparation #31) and styrene (250 mg, 2.399 mmol, Aldrich) in DCM (15 mL) was added 5% aqueous sodium hypochlorite solution (5 mL, 1.599 mmol). The reaction mixture was warmed to RT over 1 h. The reaction mixture was diluted with dichloromethane (15 mL) and washed with water (10 mL). The organic layer was dried over sodium sulphate and evaporated under reduced pressure. The residue obtained was purified by solvent washings with hexane to afford 6-chloro-2-methyl-4-(5-phenyl-4,5-dihydroisoxazol-3-yl)pyridazin-3(2H)-one 0.250 g (54%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.816 (s, 1H), 7.400-7.327 (m, 5H), 5.807-5.758 (m, 1H) 4.001-3.927 (m, 1H) 3.773 (s, 3H) 3.627-3.558 (m, 1H); MS m/z: 312.2 (M+H)+;

Workup

  1. washwashed with water (10 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe residue obtained
  5. customwas purified by solvent washings with hexane

Sources & evidence

ORD record
ord-e1078564107e4fe5bea6dc06ab447b63
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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