Pyridine → HCID 72579577, compound

HRID 2378044Notes

Reaction equation

HRID 2378044 reaction equation
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl.[NH2:31][OH:32]>C(O)C.C(OCC)(=O)C>[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:31][OH:32])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 598575951-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)-2-phenylethan-1-one2×

Product 1

HCID 72579577HCID 72579577, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring suspension consisting of 1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-phenyl-ethanone (compound A, 955 g) in ethanol (8 L) is added pyridine (4 L) and hydroxylamine hydrochloride (610 g). The resulting mixture is heated at 100° C. for two hours and subsequently stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure to afford a residue that is dissolved in ethyl acetate. The solution is washed with 5% aqueous citric acid and brine. The organic layer is separated, is dried over anhydrous Na2SO4, and is concentrated under reduced pressure. The concentrate is triturated with pentane. The triturated solids are collected by filtration to afford the solid product (480 g.) The filtrate is concentrated under reduced pressure and that concentrate is triturated with pentane. The solids are collected by filtration to provide another crop of solid product (320 g), which afforded a total of 800 g of Compound B.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto afford a residue that
  3. washThe solution is washed with 5% aqueous citric acid and brine
  4. customThe organic layer is separated
  5. dry with materialis dried over anhydrous Na2SO4
  6. concentrationis concentrated under reduced pressure
  7. customThe concentrate is triturated with pentane
  8. filtrationThe triturated solids are collected by filtration
  9. customto afford the solid product (480 g.) The filtrate
  10. concentrationis concentrated under reduced pressure
  11. customthat concentrate is triturated with pentane
  12. filtrationThe solids are collected by filtration

Sources & evidence

ORD record
ord-7dd5a7bcc66f4bd6b3c8376d9a48bf4e
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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