Sodium Nitrite → (6-Bromo-1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)(hydroxyimino)acetonitrile

HRID 1986368Notes

Reaction equation

HRID 1986368 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([CH2:17][C:18]#[N:19])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[N:20]([O-])=[O:21].[Na+]>CO.Cl>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:17](=[N:20][OH:21])[C:18]#[N:19])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 86045130(6-Bromo-1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrile

Product 1

HCID 136384883(6-Bromo-1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)(hydroxyimino)acetonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

The product from Step 5 (2.5 g, 7.99 mmol) in methanol (40 mL) and 2 N hydrochloric acid (16 mL) was treated portionwise with NaNO2 (1.10 g, 16 mmol) and allowed to stir at rt for 1 h. The resulting tan precipitate was filtered and washed with methanol to give the title compound (2.7 g, 99%). MS (ES+) m/e 342/344 [M+H]+.

Workup

  1. filtrationThe resulting tan precipitate was filtered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-ecb357f53e764bb5982f2d246c970172
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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