Formamidine acetate → 5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile

HRID 637965Notes

Reaction equation

HRID 637965 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:16]#[N:17])[C:7](=[O:15])[NH:8][C:9]=1[CH:10]=[CH:11][N:12](C)C)(=O)[CH3:2].C(O)(=O)C.C(N)=N>CN(C)C=O>[CH3:2][C:1]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:16]#[N:17])[C:7](=[O:15])[NH:8]2

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 53841137HCID 53841137, compound

Product 1

HCID 57130685-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrileYield 103.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 33.2 g of 5-acetyl-1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridincarbonitrile, 32.1 g of formamidine acetate and 300 ml of dimethylformamide was heated in a oil bath at 120°-130° C. for 3 hours, the original yellow solid dissolving and dark solution resulting. The reaction mixture was evaporated to dryness and then treated with 400 ml of water followed by 30 ml of acetic acid. The resulting insoluble solid was collected, washed with water, air-dried, recrystallized from dimethylformamide and dried at 90° C. to yield 27.4 g of 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile as a compound containing 1/2 mole of dimethylformamide, m.p. 278°-280° C. with decomposition.

Workup

  1. temperaturewas heated in a oil bath at 120°-130° C. for 3 hours
  2. dissolutionthe original yellow solid dissolving
  3. customdark solution resulting
  4. customThe reaction mixture was evaporated to dryness
  5. additiontreated with 400 ml of water
  6. customThe resulting insoluble solid was collected
  7. washwashed with water
  8. customair-dried
  9. customrecrystallized from dimethylformamide
  10. customdried at 90° C.

Sources & evidence

ORD record
ord-bc73c37009964ec6aa9e463e3ba9f20f
Source dataset
uspto-grants-1985_12
Patent number
US04559347

Reaction notes

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