Nitric Acid → HCID 57814380, compound

HRID 1677663Notes

Reaction equation

HRID 1677663 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[C:10]1([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]3[CH:22]=[N:23][CH:24]=[C:17]23)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>>[N+:6]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH:16]1[CH2:21][CH2:20][CH2:19][N:18]2[CH:22]=[N:23][CH:24]=[C:17]12)([O-:9])=[O:7]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 66933886HCID 66933886, compound

Product 1

HCID 57814380HCID 57814380, compound

Conditions

Temperature
0 °C

Procedure

0.055 ml of sulphuric acid is added slowly dropwise at 0° C. to 0.046 ml of nitric acid. The nitrating acid is subsequently added slowly dropwise at 0° C. to 0.69 mmol of 8-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine. The reaction mixture is subsequently stirred at 0° C. for 5 minutes and then poured into ice-water. The aqueous phase is rendered neutral with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (3×). The combined organic phases are dried over magnesium sulphate and evaporated. From the residue the title compound is obtained by means of flash chromatography (SiO2 60F) as a brown wax. Rf=0.25 (dichloromethane/ammonia (2M in EtOH) 97:3), Rt=5.10 (Gradient I).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-9ac8d3d3c6db432d9b93c1f42b1ee41f
Source dataset
uspto-grants-2011_08
Patent number
US08008334B2

Reaction notes

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