Nitric Acid → HCID 611779, compound

HRID 1899841Notes

Reaction equation

HRID 1899841 reaction equation
[NH:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2.[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[N+:14]([C:6]1[C:5]2[C:4]3[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:13])[C:3]=3[CH:12]=[CH:11][CH:10]=2)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 67222benz(cd)indol-2(1H)-one

Product 1

HCID 611779HCID 611779, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 33.9 g (0.200 mol) benz[cd]indol-2(1H)-one in 150 ml glacial acetic acid was added dropwise 16.5 ml (0.260 mol) nitric acid. At first, there was a very minor exotherm and then, over the course of one hour, the reaction temperature rose to 50° C. The reaction mixture was gradually cooled to room temperature with a cold water bath. A thick dark green paste resulted. This mixture was filtered, washed with 50% aqueous acetic acid, and pulled as dry as possible. The resulting wet filter cake was refluxed in 600 ml methanol and then cooled to 0° C. The mixture was filtered, washed with cold methanol and dried in vacuo to yield 22.2 g (51% theory) of 6-nitrobenz[cd]indol-2(1H)-one. TLC (CHCl3 :MeOH 95:5) showed the product to be essentially one spot material.

Workup

  1. customover the course of one hour
  2. customrose to 50° C
  3. customA thick dark green paste resulted
  4. filtrationThis mixture was filtered
  5. washwashed with 50% aqueous acetic acid
  6. customas dry as possible
  7. temperatureThe resulting wet filter cake was refluxed in 600 ml methanol
  8. temperaturecooled to 0° C
  9. filtrationThe mixture was filtered
  10. washwashed with cold methanol
  11. customdried in vacuo

Sources & evidence

ORD record
ord-72fcbb70c67046d4a2c6789d16569221
Source dataset
uspto-grants-1996_11
Patent number
US05574039

Reaction notes

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