Hydroxyamine hydrochloride → 3,5-Dibromopyridine-4-carbonitrile

HRID 1521559Notes

Reaction equation

HRID 1521559 reaction equation
[Br:1][C:2]1[CH:9]=[N:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]=O.Cl.O[NH2:13]>C(O)=O.S(=O)(=O)(O)O>[Br:1][C:2]1[CH:9]=[N:8][CH:7]=[C:6]([Br:10])[C:3]=1[C:4]#[N:13]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 27629983,5-Dibromo-4-pyridinecarboxaldehyde

Product 1

HCID 425530063,5-Dibromopyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 284Formic AcidSolvent

Procedure

To a solution of 3,5-dibromoisonicotinaldehyde (2.0 g, 0.0075 mol) in formic acid was added hydroxyl amine hydrochloride (14 mL) and concentrated sulfuric acid (5 drops) under argon atmosphere. The reaction mixture was heated to reflux for 8 h. After 8 h, the mixture was cooled to room temperature and concentrated. The residue was dissolved in diethyl ether, washed diethyl ether with saturated solution of sodium bicarbonate, water, saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated to afford the title compound. 1H NMR (400 MHz, CdCl3) δ 8.81 (s, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washwashed diethyl ether with saturated solution of sodium bicarbonate, water, saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-68993533f25b4654882ae8959e1578ee
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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