Pyridine → HCID 54497110, compound

HRID 1422358Notes

Reaction equation

HRID 1422358 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[CH:15]=O.Cl.[O:18]([NH2:20])[CH3:19].N1C=CC=CC=1>CCO.CCOC(C)=O>[CH3:19][O:18][N:20]=[CH:15][C:4]1[CH:5]=[C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:8][C:3]=1[CH2:2][OH:1]

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 521874O-Methylhydroxylamine hydrochloride2×HCID 18779202HCID 18779202, compound

Product 1

HCID 54497110HCID 54497110, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the aldehyde from step A (0.13 g, 0.61 mmol), methoxylamine hydrochloride (61 mg, 0.735 mmol) and pyridine (2 mL) in EtOH (10 mL) was heated at reflux for 16 h. Further portions of methoxylamine hydrochloride (61 mg, 0.735 mmol) and pyridine (2 mL) were added and heating was continued for 24 h. The solution was cooled, diluted with EtOAc, extracted with water (2×) then brine, dried and concentrated to give the title compound as an oil. This was used as such in the next step.

Workup

  1. temperatureat reflux for 16 h
  2. temperatureheating
  3. temperatureThe solution was cooled
  4. extractionextracted with water (2×)
  5. dry with materialbrine, dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d22cb29773c4e2ea8f084b6d124b626
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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