Pyridine → HCID 136343409, compound

HRID 562873Notes

Reaction equation

HRID 562873 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:6][C:7]=1[CH:8]=O.Cl.[NH2:17][OH:18].N1C=CC=CC=1>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:6][C:7]=1[CH:8]=[N:17][OH:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 59201291HCID 59201291, compound

Product 1

HCID 136343409HCID 136343409, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Fluoro-[2,2′]bipyridinyl-6-carbaldehyde (0.36 mmol, 73 mg), hydroxylamine hydrochloride (1.8 mmol, 125 mg), pyridine (1.6 mmol, 0.12 mL) and EtOH were heated at reflux during 2 h. The solvent was evaporated under vacuum, and H2O was added. The filtration of the white precipitate obtained provided the final product without needing any purification (Florence Mongin; Francois Trecourt; Bruno Gervais; Oliver Mongin; Guy Quequiner, J. Org. Chem., 2002, 67, 3272-3276). Yield: 47 mg (60%), white solid. 1H-NMR (DMSO): 12.0 (N—OH); 8.76 (d, 1H, J=4.4 Hz); 8.46 (dd, 1H, J1=8.5 Hz, J1=3.4 Hz); 8.40 (d, 1H, J=7.9 Hz); 8.34 (s, 1H); 8.01 (m, 2H); 7.54 (m, 1H)

Workup

  1. temperatureat reflux during 2 h
  2. customThe solvent was evaporated under vacuum, and H2O
  3. additionwas added
  4. filtrationThe filtration of the white precipitate
  5. customobtained

Sources & evidence

ORD record
ord-247b9ade474045a0ae8d8a281d2321aa
Source dataset
uspto-grants-2011_11
Patent number
US08067441B2

Reaction notes

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