Methanol → HCID 18980351, compound

HRID 2392716Notes

Reaction equation

HRID 2392716 reaction equation
[C:1]1(Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[Cl:19])[NH:15][C:14](=[O:20])[CH:13]=[N+:12]2[O-:21].CO>C1COCC1>[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[Cl:19])[NH:15][C:14](=[O:20])[C:13]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[N+:12]2[O-:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 7961BromobenzeneHCID 18980356HCID 18980356, compound

Product 1

HCID 18980351HCID 18980351, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Grignard reagent prepared from Mg (240 mg, 10 mmol) and phenyl bromide (10 mmol) in THF (50 mL) solid powdered nitrone 124 (2 mmol) was added in small portions. The mixture was stirred for 2 h, then decomposed with MeOH (50 mL) and evaporated. The crude hydroxylamine derivative 139 was washed with hexane (3×10 mL), suspended in CHCl3 (100 mL) and stirred with MnO2 for 16 h. Solid inorganic material was filtered off, washed with CHCl3 (10×10 mL), and MeOH (10×10 mL). Combined organic filtrate was evaporated. Solid residue was chromatographed on prep. TLC plate, eluent--mixture CHCl3 --MeOH (15:1), to yield of 3-aryl nitrone 126. Yield: 39%; the compound was identical to that prepared in Example 6.

Workup

  1. additionwas added in small portions
  2. customevaporated
  3. washThe crude hydroxylamine derivative 139 was washed with hexane (3×10 mL)
  4. stirringstirred with MnO2 for 16 h
  5. filtrationSolid inorganic material was filtered off
  6. washwashed with CHCl3 (10×10 mL), and MeOH (10×10 mL)
  7. customCombined organic filtrate was evaporated
  8. customSolid residue was chromatographed on prep
  9. customthat prepared in Example 6

Sources & evidence

ORD record
ord-023968dc7234497f903efa5a21887f35
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

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