Pyridine → HCID 18446923, compound

HRID 1726389Notes

Reaction equation

HRID 1726389 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.[O:13]([NH2:15])[CH3:14].N1C=CC=CC=1>C(O)C>[CH3:14][O:13]/[N:15]=[C:7]1\[CH2:6][CH2:5][C:4]2[C:8]\1=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 5206955-Bromo-1-indanoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 18446923HCID 18446923, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5-bromoindanone (6.03 g) in 40 mL ethanol was added 3.58 g methoxylamine hydrochloride and 3.5 mL pyridine. The mixture was stirred at ambient temperature for 1 hour and heated at 80° C. for 3 hours. The volatiles were removed under vacuum and the solid residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The ethyl acetate was washed with brine, dried over magnesium sulfate, filtered, and evaporated under vacuum to yield 6.74 g (98% yield) of a tan solid. 1H NMR (CDCl3) was consistent with an isomeric mixture of the desired structure, with the E oxime isomer as the major component. LC/MS indicated 2 close peaks, both with a M+1 molecular ion of m/z 242.0 by positive ESI.

Workup

  1. temperatureheated at 80° C. for 3 hours
  2. customThe volatiles were removed under vacuum
  3. customthe solid residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. washThe ethyl acetate was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-6154153a703f4fd0ba7551b858792695
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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