Sulfuric Acid → 5-Methyl-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxamide

HRID 637967Notes

Reaction equation

HRID 637967 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[N:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[C:10]([C:18]#[N:19])[C:11](=[O:17])[NH:12]2.[OH-:20].[NH4+]>C(O)(=O)C>[CH3:6][C:7]1[N:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[C:10]([C:18]([NH2:19])=[O:20])[C:11](=[O:17])[NH:12]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 57130685-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile

Product 1

HCID 132320465-Methyl-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 200 ml of concentrated sulfuric acid chilled in an ice bath was added with stirring 37 g of 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile and the reaction mixture was allowed to stand at room temperature overnight. The reaction mixture was then poured on ice (1 liter beaker, half filled), the resulting mixture cooled in an ice bath and then neutralized by adding aqueous ammonium hydroxide, followed by addition of acetic acid to make the mixture slightly acidic. The separated solid was collected, washed with water, air-dried, then recrystallized from a large volume of dimethylformamide (1.2 1.) and dried at 95° C. to yield 28.4 g of 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carboxamide, m.p.>320° C.

Workup

  1. additionwas added
  2. additionThe reaction mixture was then poured on ice (1 liter beaker, half filled)
  3. temperaturethe resulting mixture cooled in an ice bath
  4. customThe separated solid was collected
  5. washwashed with water
  6. customair-dried
  7. customrecrystallized from a large volume of dimethylformamide (1.2 1.)
  8. customdried at 95° C.

Sources & evidence

ORD record
ord-aeb0f746bfbd4c34ba40371d9a4c16b0
Source dataset
uspto-grants-1985_12
Patent number
US04559347

Reaction notes

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