Sodium Nitrate → 6-Hydroxy-8-(3-nitrophenyl)-1,7-naphthyridine

HRID 369026Notes

Reaction equation

HRID 369026 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N+]([O-])([O-])=[O:22].[Na+]>S(=O)(=O)(O)O.O>[OH:22][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 24268Sodium NitrateHCID 106117788-(3-Nitrophenyl)-1,7-naphthyridin-6-amine

Product 1

HCID 1785266086-Hydroxy-8-(3-nitrophenyl)-1,7-naphthyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-amino-8-(3-nitrophenyl)-1,7-naphthyridine (500 mg, 1.87 mmol; prepared according to example 1) in concentrated sulfuric acid and water (3 ml, 2:1) is added sodium nitrate (155 mg, 2.25 mmol) at 4° C. After 30 minutes, the ice bath is removed, and the mixture is warmed to 70° C. for 30 minutes. the reaction mixture is poured onto ice, and the solution is neutralized by adding sodium bicarbonate. The precipitate is filtered and washed with water affording the title compound. mp 262-265° C.

Workup

  1. customthe ice bath is removed
  2. additionthe reaction mixture is poured onto ice
  3. additionby adding sodium bicarbonate
  4. filtrationThe precipitate is filtered
  5. washwashed with water affording the title compound

Sources & evidence

ORD record
ord-40f86e8d87714ff2b67d778d1673ea64
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Reaction notes

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