Sodium Carbonate → HCID 89462835, compound

HRID 1525216Notes

Reaction equation

HRID 1525216 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.Cl.[OH:17][NH2:18].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:18][OH:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 20145702HCID 20145702, compound2×

Product 1

HCID 89462835HCID 89462835, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (6-bromopyridin-3-yl)(phenyl)methanone, 4-b, (5.2 g, 20 mmol) in 100 ml of 95% ethanol was treated with N-hydroxylamine hydrochloride (4.2 g, 60 mmol) and sodium carbonate (6.36 g, 60 mmol). The resulting mixture was heated at reflux for 3 hours, cooled to room temperature, and concentrated under vacuum. The residue was taken into ethyl acetate (100 mL) followed by washing with water and brine (50 mL each). The organic layer was dried over sodium sulfate and concentrated. The resulting solid was recrystallized in ethyl acetate/petroleum ether to provide the product, 4-c, (2.7 g, 50%). 1H NMR (CD3OD, 300 MHz,): δ 8.34 (s, 1H), 7.78 (m, 1H), 7.32 (m, 7H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated under vacuum
  4. washby washing with water and brine (50 mL each)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting solid was recrystallized in ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-9d12023385564e5c8f2ffb6e29538e80
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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