Hydrogen Bromide → HCID 178466647, compound

HRID 1952864Notes

Reaction equation

HRID 1952864 reaction equation
C([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[O:12])[CH3:11])[N:5]=1)C.Br.[OH-].[Na+]>>[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[O:12])[CH3:11])[N:5]=1

Participants

4

Reactant 3

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 15390057HCID 15390057, compound

Product 1

HCID 178466647HCID 178466647, compound

Conditions

Temperature
95 °C

Procedure

48.5 g of 2-ethoxy-6-acetylpyridine were introduced into 145 ml of hydrogen bromide solution (30 percent strength solution in glacial acetic acid) and the mixture was heated to 95° C. A further 176 ml of hydrogen bromide solution (30% strength solution in glacial acetic acid) were added dropwise at this temperature. The mixture was stirred for 3 hours at 95° C. and then cooled to room temperature. It was poured into ice-water and neutralized to pH 7 using 50 percent strength aqueous sodium hydroxide solution. The mixture was subsequently extracted 3 times with methyl tert-butyl ether. The aqueous phase was concentrated. The residue which remained was stirred 4 times with acetone. After the combined acetone phases had been concentrated, there remained 38.5 g of 2-hydroxy-6-acetylpyridine as a colorless solid (m.p.: 115-117 C).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was subsequently extracted 3 times with methyl tert-butyl ether
  3. concentrationThe aqueous phase was concentrated
  4. stirringThe residue which remained was stirred 4 times with acetone
  5. concentrationAfter the combined acetone phases had been concentrated

Sources & evidence

ORD record
ord-8269b40d6e1e4727b9953e615601b9de
Source dataset
uspto-grants-2000_09
Patent number
US06114363

Reaction notes

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