Hydroxyamine hydrochloride → 4-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime

HRID 475230Notes

Reaction equation

HRID 475230 reaction equation
[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:17]=O.CC([O-])=O.[Na+].Cl.[NH2:25][OH:26]>CO>[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:17]=[N:25][OH:26]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866947324-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde

Product 1

HCID 866947334-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oximeYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 148 (7.7 g, 0.031 mol) in dry MeOH (120 mL) was added NaOAc (3.31 g, 0.0372 moles) and hydroxylamine hydrochloride (2.57 g, 0.0372 mol). The reaction mixture was stirred at RT for 16 h. The solution was concentrated in vacuo, the residue taken up in water and extracted with DCM. The combined organic extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 5.8 g (71%) of 4-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime (150) as a white solid which was used without further purification.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. extractionextracted with DCM
  3. washThe combined organic extracts were washed sequentially with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eece803e4ce342d5babeb597c9918e54
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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