Sulfuric Acid → 5-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 648377Notes

Reaction equation

HRID 648377 reaction equation
[C:1]([C:4]1[CH:12]=[C:8]([C:9](N)=[O:10])[C:7](=[O:13])[NH:6][C:5]=1[CH3:14])(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:16]>O>[C:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:16])=[O:10])[C:7](=[O:13])[NH:6][C:5]=1[CH3:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 27644175-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 132320405-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 34 g of 5-acetyl-1,2-dihydro-6-methyl-2-oxonicotinamide, 50 ml of concentrated sulfuric acid and 100 ml of water was heated on a steam bath with stirring for 6 hours. The hot reaction solution was filtered and to the filtrate was added 50 ml of water. The resulting mixture was allowed to stand at room temperature overnight whereupon the product crystallized out. The separated product was collected, washed with water, dried in a vacuum oven at 90°-95° C. to yield 16.8 g of 5-acetyl-1,2-dihydro-6-methyl-2-oxonicotinic acid, m.p. 238°-241° C. This acid was recrystallized from methanol and dried to yield 14.7 g of 5-acetyl-1,2-dihydro-6-methyl-2-oxonicotinic acid, m.p. 241°-243° C.

Workup

  1. temperaturewas heated on a steam bath
  2. filtrationThe hot reaction solution was filtered and to the filtrate
  3. additionwas added 50 ml of water
  4. waitto stand at room temperature overnight whereupon the product
  5. customcrystallized out
  6. customThe separated product was collected
  7. washwashed with water
  8. customdried in a vacuum oven at 90°-95° C.

Sources & evidence

ORD record
ord-34642828fd204cf4a28bb7835be44850
Source dataset
uspto-grants-1983_10
Patent number
US04412077

Reaction notes

Loading…