Sodium Nitrite → 1-(6-Bromopyridin-2-yl)-2-hydroxyethanone

HRID 385807Notes

Reaction equation

HRID 385807 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=1)=[O:4].N([O-])=[O:13].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Br:11][C:7]1[N:6]=[C:5]([C:3](=[O:4])[CH2:2][OH:13])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 534075852-Bromo-1-(6-bromopyridin-2-yl)ethan-1-one

Product 1

HCID 595256021-(6-Bromopyridin-2-yl)-2-hydroxyethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-1-(6-bromopyridin-2-yl)ethanone (500 mg, 1.79 mmol) in dimethylformamide (11.5 mL) was added sodium nitrite (124 mg, 1.79 mmol). After 14 hours, the reaction was diluted with ethyl acetate (200 mL) and washed with saturated aqueous sodium bicarbonate (100 mL), water (2×100 mL), and brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to give the title compound. 1H NMR (600 MHz, DMSO): δ 7.94 (m, 2H), 7.91 (m, 1H), 5.07 (t, J=5.9 Hz, 1H), 4.85 (d, J=5.9 Hz, 2H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (100 mL), water (2×100 mL), and brine (100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-21b2ff68390e43bca80ee7e83ad21641
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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