Sulfuric Acid → 5-(Diphenylmethyl)-2-pyridone

HRID 1390324Notes

Reaction equation

HRID 1390324 reaction equation
[CH:1](O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.S(=O)(=O)(O)O>>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:19]2[CH:20]=[CH:21][C:16](=[O:15])[NH:17][CH:18]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7037BenzhydrolHCID 178516071HCID 178516071, compound

Product 1

HCID 227488105-(Diphenylmethyl)-2-pyridone

Procedure

To a mixture of 92.1 g (0.5 mole) of benzhydrol and 142.7 g. (1.5 mole) of 2-hydroxypyridine heated at 180°, add with stirring 1.5 ml. of concentrated sulfuric acid. Heat the mixture at 250°-255° for 2 hours with the removal of water. Pour the cooled reaction mixture into water, stir, and extract with chloroform. Concentrate the chloroform extracts to a residue containing 5-(diphenylmethyl)-2-pyridone. Triturate the residue with ethyl acetate and filter the solids to obtain 5-(diphenylmethyl)-2-pyridone plus other isomers. Recrystallize from acetonitrile to obtain the product of this example, m.p. 174°-176° C.

Workup

  1. additionadd
  2. temperatureHeat the mixture at 250°-255° for 2 hours
  3. customwith the removal of water
  4. additionPour
  5. customthe cooled reaction mixture into water
  6. stirringstir
  7. extractionextract with chloroform
  8. concentrationConcentrate the chloroform
  9. additioncontaining 5-(diphenylmethyl)-2-pyridone
  10. customTriturate the residue with ethyl acetate
  11. filtrationfilter the solids

Sources & evidence

ORD record
ord-f03122b6954441ab951c2bb55efe943e
Source dataset
uspto-grants-1979_02
Patent number
US04138488

Reaction notes

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