Hydroxyamine hydrochloride → 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oxime

HRID 2409052Notes

Reaction equation

HRID 2409052 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[N:14][C:15]([C:17](=O)[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:5][CH:4]=1.CC([O-])=O.[Na+].Cl.[NH2:28][OH:29]>CO>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[N:14][C:15]([C:17](=[N:28][OH:29])[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866898611-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone

Product 1

HCID 1364091021-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oximeYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone (500 mg, 1.78 mmol) and NaOAc (1.21 g, 17.80 mmol) in MeOH (10 mL) at RT was added hydroxylamine hydrochloride (618 mg, 8.90 mmol). The reaction was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure. To the residue was added water (100 mL) followed by extraction with EtOAc (50 mL×3). The combined extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford 320 mg (61%) of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oxime as a yellow solid. MS (ESI): m/z=297.2 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added water (100 mL)
  3. extractionfollowed by extraction with EtOAc (50 mL×3)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef181a5caa6947b5a09ba2e79c58c601
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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