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

HRID 637958
Notes
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Reaction equation

HRID 637958 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-08b661d5643b4b5cae360e1cfde66ba1
Source dataset
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04559347

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes