Nitric Acid → HCID 53708919, compound

HRID 459876Notes

Reaction equation

HRID 459876 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C@@:2]21[CH:14]1[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]1)[CH2:10]2.[N+:17]([O-])([OH:19])=[O:18].O.C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[N+:17]([C:8]1[CH:9]=[C:4]2[CH2:3][C@:2]3([CH:14]4[CH2:13][CH2:12][N:11]([CH2:16][CH2:15]4)[CH2:10]3)[O:1][C:5]2=[N:6][CH:7]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 9794392Azd0328

Product 1

HCID 53708919HCID 53708919, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

(R)-(−)-Spiro[1-azabicyclo[2.2.2]octane-3,2′ (3′H)-furo[2,3-b]pyridine] (3.03 g, 14 mmol) was dissolved in concentrated sulfuric acid (7 ml) at 0–5° C., fuming nitric acid (3.3 ml, 70.2 mmol) was added over 10 minutes, the mixture was stirred for 1 hour, and heated at 65–70° C. for 24 hours, cooled, poured onto ice (200 g), added 300 ml of water, basified to pH 10 with solid potassium carbonate, stirred for 1 hour, filtered off and dried, provided the solid title compound (3.6 g, 13.8 mmol, 98%): electrospray MS 262 ([MH]+, 100).

Workup

  1. temperatureheated at 65–70° C. for 24 hours
  2. temperaturecooled
  3. additionpoured onto ice (200 g)
  4. stirringstirred for 1 hour
  5. filtrationfiltered off
  6. customdried

Sources & evidence

ORD record
ord-5ce398bbb68e435c87a3dc7899356771
Source dataset
uspto-grants-2007_03
Patent number
US07196096B2

Reaction notes

Loading…