Nitric Acid → HCID 178526831, compound

HRID 1725515Notes

Reaction equation

HRID 1725515 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH:4]=[CH:3][NH:2]1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[N+:12]([C:4]1[C:5]2[C:10](=[CH:9][N:8]=[CH:7][CH:6]=2)[C:1]([OH:11])=[N:2][CH:3]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 8201511,2-Dihydro-2,7-naphthyridin-1-one

Product 1

HCID 178526831HCID 178526831, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 2H-[2,7]naphthyridin-1-one (300 mg, 2.05 mmol) (Baldwin, J. J.; Mensler, K.; Ponticello, G. S, J. Org. Chem. 1978, 43(25), 4878-80.) in 98% sulfuric acid (2 ml), 60% nitric acid (0.30 ml) was added dropwise and the mixture was warmed to 85° C. during 3 h. Addition, of ice-cold water and basification to pH 7, gave a precipitate which was filtered and washed with ethyl ether to yield the title product as a yellow solid (87%).

Workup

  1. additionAddition
  2. customof ice-cold water and basification to pH 7, gave a precipitate which
  3. filtrationwas filtered
  4. washwashed with ethyl ether

Sources & evidence

ORD record
ord-9daabb9ffc88463a967242b15c16efca
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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