Pyridine → HCID 87625407, compound

HRID 1726390Notes

Reaction equation

HRID 1726390 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.Cl.[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>C(O)C>[CH2:13]([O:20]/[N:21]=[C:7]1\[CH2:6][CH2:5][C:4]2[C:8]\1=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 102312Benzyloxyamine hydrochlorideHCID 5206955-Bromo-1-indanone

Product 1

HCID 87625407HCID 87625407, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5-bromoindanone (5.66 g) in 60 mL ethanol was added 5.57 g O-benzylhydroxylamine hydrochloride and 3.2 mL pyridine. The mixture was stirred at ambient temperature for 5 hours. The volatiles were removed under vacuum and the solid residue partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The ethyl acetate was washed with brine, dried over magnesium sulfate, filtered, and evaporated under vacuum to afford crude product as an amber oil. The crude material was crystallized from hexane to afford 5.43 g (84% yield) light tan solid. 1H NMR (CDCl3) was consistent with the desired product. LC/MS indicated a single peak with a M+1 molecular ion of m/z 318.1 by positive ESI.

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe solid residue partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  3. washThe ethyl acetate was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto afford crude product as an amber oil
  8. customThe crude material was crystallized from hexane
  9. customto afford 5.43 g (84% yield) light tan solid

Sources & evidence

ORD record
ord-806717fb96374f668d86a0b2dee4ff10
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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