Nitric Acid → 8-Nitro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one

HRID 1936985Notes

Reaction equation

HRID 1936985 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH2:10]1[CH:22]2[CH:13]([C:14](=[O:23])[NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=32)[CH2:12][CH2:11]1>ClCCl>[N+:1]([C:19]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:23])[CH:13]3[CH2:12][CH2:11][CH2:10][CH:22]3[C:21]=2[CH:20]=1)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 154282261,2,3,3a,5,9b-Hexahydrocyclopenta[c]quinolin-4-one

Product 1

HCID 224624498-Nitro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-oneYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

65% Nitric acid (0.33 ml) is mixed at 0° C. with 96% sulfuric acid (0.44 ml). To this end, a solution of 1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one (1.9 g, 5.3 mmol) in dichloromethane (5 ml) is added in drops. After 1 hour at room temperature, the batch is poured onto ice water, the solid is filtered off and washed with water. Column-chromatographic purification (SiO2) of the filter residue with ethyl acetate-hexane yields 0.65 g (53%) of product.

Workup

  1. additionthe batch is poured onto ice water
  2. filtrationthe solid is filtered off
  3. washwashed with water
  4. customColumn-chromatographic purification (SiO2) of the filter residue with ethyl acetate-hexane

Sources & evidence

ORD record
ord-95ff8e31f78141f4a608cb29377efec6
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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