Nitric Acid → HCID 11458385, compound

HRID 1633725Notes

Reaction equation

HRID 1633725 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>O>[N+:18]([C:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 70003Benzosuberone

Product 1

HCID 11458385HCID 11458385, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6,7,8,9-Tetrahydro-5H-benzo[a]cyclohepten-5-one (18.5 g, 11.5 mmol) was mechanically stirred at −15° C. and treated with concentrated sulfuric acid (41 mL) over 5 minutes, stirred 10 minutes, treated dropwise over 10 minutes with a mixture of fuming nitric acid (9 mL) and concentrated sulfuric acid (14 mL), stirred at −15° C. for 15 minutes and poured carefully onto a mixture of ice (200 g) and water (200 mL). The resulting solid was collected by filtration, washed with water (100 mL, 2×), dried and recrystallized from ethanol (200 mL). The resulting solid was removed by filtration and the filtrate was suspended on silica gel and purified on silica gel eluting with ethyl acetate:hexanes 12:88 to provide the desired product.

Workup

  1. stirringstirred at −15° C. for 15 minutes
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water (100 mL, 2×)
  4. customdried
  5. customrecrystallized from ethanol (200 mL)
  6. customThe resulting solid was removed by filtration
  7. custompurified on silica gel eluting with ethyl acetate:hexanes 12:88

Sources & evidence

ORD record
ord-2901ce168caf43a8bfc653d10653952c
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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