Nitric Acid → HCID 18983889, compound

HRID 1440467Notes

Reaction equation

HRID 1440467 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]2[CH:19]=1)=[O:5])[CH3:2].[N+:20]([O-])([OH:22])=[O:21].[OH-].[Na+]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]2[C:19]=1[N+:20]([O-:22])=[O:21])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 189838522,8-Diethyl imidazo[1,2-a]pyridine-2,8-dicarboxylate

Product 1

HCID 18983889HCID 18983889, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Ethyl 2-ethoxycarbonylimidazo[1,2-a]pyridine-8-carboxylate (3.8 g, 14.5 m mol) was dissolved in conc. sulfuric acid (10 ml), and to the solution was slowly added 70% nitric acid (1.5 ml) at 10° C. The mixture was stirred at room temperature for 30 minutes, poured into ice water and adjusted to pH 7 by adding 20% sodium hydroxide. The precipitated crystals were filtered to obtain ethyl 2-ethoxycarbonyl-3-nitro-imidazo[1,2-a]pyridine-8-carboxylate (2.4 g, yield 53.8%) as crystals of m.p. 139°-140° C. A solution of the crystals in conc. hydrochloric acid (35 ml) was refluxed for 1.5 hours and cooled to room temperature. The precipitated crystals were collected by filtration and dried to give the object compound (1.2 g, yield 74.3%) of m.p.>300° C.

Workup

  1. customat 10° C
  2. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-d8d857799f544678a0ac714e1dabf544
Source dataset
uspto-grants-1996_03
Patent number
US05498774

Reaction notes

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