Nitric Acid → HCID 67264550, compound

HRID 1040609Notes

Reaction equation

HRID 1040609 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]12[O:16][CH:12]([CH2:13][NH:14][CH2:15]1)[C:11]1[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[N+:1]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:12]1[O:16][CH:5]2[CH2:15][NH:14][CH2:13]1)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 14208733HCID 14208733, compound

Product 1

HCID 67264550HCID 67264550, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Concentrated nitric acid (10 mL) was added to a mixture of 12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (5.1 g, 32 mmol) and concentrated sulfuric acid (10 mL) at 0° C. The resulting solution was stirred at 0° C. for 30 min before pouring onto ice, adding 10 N NaOH slowly until basic, and extracting with CH2Cl2 (2×25 mL). The combined organic layers were dried over MgSO4, filtered, concentrated and purified with silica gel chromatography (0-30% MeOH in CH2Cl2) to obtain 4-Nitro-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene as a gummy, brown oil (4.2 g, 65%). MS (m/e) 207 (M+1).

Workup

  1. additionbefore pouring onto ice
  2. extractionextracting with CH2Cl2 (2×25 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified with silica gel chromatography (0-30% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a680f1c68bf34b9783ba9462b565c286
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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