Nitric Acid → HCID 46205076, compound

HRID 1951337Notes

Reaction equation

HRID 1951337 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=12.[N+:12]([O-:15])(O)=[O:13].[C:16]([O-])([O-])=O.[Na+].[Na+]>S(=O)(=O)(O)O>[CH3:16][C:2]1[N:1]=[C:5]2[C:6]([CH:10]=[O:11])=[CH:7][CH:8]=[CH:9][N:4]2[C:3]=1[N+:12]([O-:15])=[O:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 10997174Imidazo(1,2-a)pyridine-8-carbaldehyde

Product 1

HCID 46205076HCID 46205076, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cooled solution of 4a (149 mg, 0.93 mmol) in concentrated sulfuric acid (4 mL), was added nitric acid (155 μl, d=1.38). After being stirred for 3 h at room temperature, the solution is crushed on ice (10g), made basic by the addition of aqueous saturated Na2CO3 solution (45 mL) and extracted with CH2Cl2. The organic layers were dried (MgSO4), filtered and evaporated to dryness to give 4m (171 mg, 90%); mp 182-184° C.; IR (KBr) 1698, 1380, 1134 cm−1; 1H NMR (400 MHz, CDCl3) δ 2.95 (s, 3H), 7.40 (t, 1H, J=7 Hz), 8.21 (d, 1H, J=7 Hz), 9.66 (d, 1H, J=7 Hz), 10.83 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 17.4, 115.7, 123.4, 130.3, 130.4, 131.9, 144.3, 152.0, 187.3; MS m/z 205 (M+, 31), 177 (100), 104 (40), 78 (37), 51 (33).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-568df2db5a664cfbbd087b79d23bd464
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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