5-(4-methoxybenzoyl)-6-methyl-2(1H)-pyridinone → 5-(4-hydroxybenzoyl)-6-methyl-2(1H)-pyridinone

HRID 638198Notes

Reaction equation

HRID 638198 reaction equation
C[O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[NH:13][C:14]=2[CH3:15])=[O:8])=[CH:5][CH:4]=1>Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[NH:13][C:14]=2[CH3:15])=[O:8])=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 217799405-(4-methoxybenzoyl)-6-methyl-2(1H)-pyridinone

Product 1

HCID 202536305-(4-hydroxybenzoyl)-6-methyl-2(1H)-pyridinoneYield 93.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture containing 13 g of 5-(4-methoxybenzoyl)-6-methyl-2(1H)-pyridinone and 100 ml of 48% aqueous hydrogen bromide solution was refluxed for 7 hours and then allowed to stand at room temperature overnight. The reaction mixture was concentrated to dryness on a rotary evaporator. To the residue was added 100 ml of water and the aqueous mixture was neutralized by adding aqueous ammonium hydroxide solution. The solid was collected, washed with water and air dried. The solid was recrystallized from 100 ml of ethanol and dried at 80°-85° C. to yield 11.4 g of 5-(4-hydroxybenzoyl)-6-methyl-2(1H)-pyridinone, m.p. 280°-282° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. concentrationThe reaction mixture was concentrated to dryness on a rotary evaporator
  3. additionTo the residue was added 100 ml of water
  4. additionby adding aqueous ammonium hydroxide solution
  5. customThe solid was collected
  6. washwashed with water and air
  7. customdried
  8. customThe solid was recrystallized from 100 ml of ethanol
  9. customdried at 80°-85° C.

Sources & evidence

ORD record
ord-fa57b6e213484d2ebf0a7cfefa7d9fbf
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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