Ammonia → 6-Methylpyridine-2,4-diol

HRID 1690212Notes

Reaction equation

HRID 1690212 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=O)[CH:3]=1.C(O)C.[NH3:13].C(Cl)(Cl)Cl>CCOCC>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:13][C:4](=[O:5])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 6212ChloroformHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 546914196-Methylpyridine-2,4-diolYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Hydroxy-6-methyl-2H-pyran-2-one (11.1 g, 88.0 mmol) was suspended into ethanol (5.0 mL), added with 28% aqueous ammonia (55 mL), and the resultant mixture was stirred at 100° C. for 1 hour. The reaction solution was cooled down to room temperature, added with chloroform (25 mL) and ether (25 mL) to extract solid substance which was then washed sequentially with chloroform (10 mL), ether (10 mL) and tetrahydrofuran (30 mL), and concentrated in vacuo. Then, the obtained residue was further washed sequentially with chloroform (10 mL), ether (10 mL) and tetrahydrofuran (30 mL). 4-Hydroxy-6-methylpyridin-2(1H)-one (9.70 g, yield 88%) was obtained as a pale yellow crystal.

Workup

  1. extractionto extract solid substance which
  2. washwas then washed sequentially with chloroform (10 mL), ether (10 mL) and tetrahydrofuran (30 mL)
  3. concentrationconcentrated in vacuo
  4. washThen, the obtained residue was further washed sequentially with chloroform (10 mL), ether (10 mL) and tetrahydrofuran (30 mL)

Sources & evidence

ORD record
ord-d6b7cef893fc40af88ac0caeb5558632
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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