Nitric Acid → 5-Iodo-6-nitro-1,2,3,4-tetrahydro-1,8-naphthyridine

HRID 1499475Notes

Reaction equation

HRID 1499475 reaction equation
[N+:1]([O-:4])(O)=[O:2].[I:5][C:6]1[CH:15]=[CH:14][N:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][NH:11]2.[OH-].[Na+]>S(=O)(=O)(O)O>[I:5][C:6]1[C:15]([N+:1]([O-:4])=[O:2])=[CH:14][N:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][NH:11]2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 577562535-Iodo-1,2,3,4-tetrahydro-1,8-naphthyridine

Product 1

HCID 867267115-Iodo-6-nitro-1,2,3,4-tetrahydro-1,8-naphthyridineYield 43.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Fuming nitric acid (0.5 mL, 10 mmol) was added a mixture of 5-iodo-1,2,3,4-tetrahydro-1,8-naphthyridine (1.0 g, 3.8 mmol) in sulfuric acid (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred for 30 min. The mixture was poured into ice-water and neutralized with 3 M aq. NaOH. The resulting solid precipitate was collected by filtration, washed with water and dried to give the sub-title compound (0.50 g, 43%). LCMS calc. for C8H9IN3O2(M+H)+: m/z=306.0. Found: 306.1.

Workup

  1. filtrationThe resulting solid precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-c0e6dd195d2f48079e2d115465f15664
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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