Ammonium Hydroxide → (9S)-9-ethyl-3-hydroxy-6-nitro-7,8,9,10-tetrahydropyrido[3,4-f]quinoxalin-9-ium-2-olate

HRID 48225Notes

Reaction equation

HRID 48225 reaction equation
[CH2:1]([N:3]1[CH2:16][CH2:15][C:14]2[CH:13]=[CH:12][C:11]3[NH:10][C:9](=[O:17])[C:8](=[O:18])[NH:7][C:6]=3[C:5]=2[CH2:4]1)[CH3:2].[N+:19]([O-])([O-:21])=[O:20].[K+].[OH-].[NH4+]>S(=O)(=O)(O)O>[CH2:1]([N:3]1[CH2:16][CH2:15][C:14]2[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:11]3[NH:10][C:9](=[O:17])[C:8](=[O:18])[NH:7][C:6]=3[C:5]=2[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 103772169-Ethyl-1,4,7,8,9,10-hexahydro-pyrido[3,4-f]quinoxaline-2,3-dione

Product 1

HCID 10266209(9S)-9-ethyl-3-hydroxy-6-nitro-7,8,9,10-tetrahydropyrido[3,4-f]quinoxalin-9-ium-2-olateYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 9-ethyl-1,4,7,8,9,10-hexahydro-pyrido[3,4-f]quinoxaline-2,3-dione (0.61 g, 2.16 mmol) in 20 mL of concentrated sulfuric acid was treated with a solution of potassium nitrate (0.25 g, 2.47 mmol) in 2 mL concentrated sulfuric acid. After stirring for 3 hours at room temperature, the reaction mixture was poured onto ice and cooled in an isopropyl alcohol/dry ice bath. Ammonium hydroxide was added to adjust the pH to 8.9, and the yellow solid was collected by filtration (0.59 g, 94% yield).

Workup

  1. additionthe reaction mixture was poured onto ice
  2. temperaturecooled in an isopropyl alcohol/dry ice bath
  3. filtrationthe yellow solid was collected by filtration (0.59 g, 94% yield)

Sources & evidence

ORD record
ord-18f874e2003043abb027aaa33ab84959
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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