Sodium amide → 2-Amino-4-methyl-3-pyridinol

HRID 2397850Notes

Reaction equation

HRID 2397850 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8].[NH2-:9].[Na+]>>[NH2:9][C:4]1[C:3]([OH:8])=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 24533Sodium amideHCID 27629084-Methylpyridin-3-ol

Product 1

HCID 5800542-Amino-4-methyl-3-pyridinol

Procedure

A mixture of 218.0 g of 4-methyl-3-pyridinol and 78.0 g of sodium amide are placed in a pressure vessel and heated at 150° for 6 hours. The vessel is allowed to cool, the solid mass is removed and added portionwise to 1 l. of cold 2-propanol. Subsequently, 20% aqueous acetic acid is added until the pH is 5.5 and the whole concentrated to dryness in vacuo. The residue is extracted thoroughly with chloroform and the chloroform extracts washed with saturated aqueous sodium chloride, dried and concentrated. The residue is fractionally crystallized from ethyl acetate to give 2-amino-4-methyl-3-pyridinol.

Workup

  1. customare placed in a pressure vessel
  2. temperatureheated at 150° for 6 hours
  3. temperatureto cool
  4. customthe solid mass is removed
  5. additionadded portionwise to 1 l
  6. additionSubsequently, 20% aqueous acetic acid is added until the pH is 5.5
  7. concentrationthe whole concentrated to dryness in vacuo
  8. extractionThe residue is extracted thoroughly with chloroform
  9. washthe chloroform extracts washed with saturated aqueous sodium chloride
  10. customdried
  11. concentrationconcentrated
  12. customThe residue is fractionally crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e7dbf053be1a4949880a8128c913112a
Source dataset
uspto-grants-1977_05
Patent number
US04022897

Reaction notes

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