Nitric Acid → HCID 178526758, compound

HRID 44786Notes

Reaction equation

HRID 44786 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[CH:7][CH:8]=[N:9]2)=[N:4][CH:3]=1.[OH-].[Na+].[N+:15]([O-])([OH:17])=[O:16]>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=[N:9]2)=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 178516370HCID 178516370, compound

Product 1

HCID 178526758HCID 178526758, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 7-bromo[1,5]naphthyridin-4-ol (33 g, 0.147 mol) and fuming nitric acid (350 mL) was heated at reflux (90° C. internal reaction vessel temperature) for 3 hours. The reaction mixture was cooled to 50° C., poured over 1 L of ice and neutralized to pH 2-3 with a solution of 50% aqueous NaOH. The resulting precipitate was filtered, washed with water, and dried over vacuum for 3 days to yield 25.1 g of 7-bromo-3-nitro[1,5]naphthyridin-4-ol as a yellow crystalline solid.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to 50° C.
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried over vacuum for 3 days

Sources & evidence

ORD record
ord-d0e8a8134ece44b5b765280cd6098265
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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