Nitric Acid → HCID 11439787, compound

HRID 1870213Notes

Reaction equation

HRID 1870213 reaction equation
[O:1]=[C:2]1[C:11](=[O:12])[NH:10][C:9]2[C:4](=[CH:5][C:6]([N:13]3[CH:17]=[CH:16][N:15]=[CH:14]3)=[CH:7][CH:8]=2)[N:3]1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].[OH-].[Na+].[N+:26]([O-])([OH:28])=[O:27]>>[O:1]=[C:2]1[C:11](=[O:12])[NH:10][C:9]2[C:4](=[CH:5][C:6]([N:13]3[CH:17]=[CH:16][N:15]=[CH:14]3)=[C:7]([N+:26]([O-:28])=[O:27])[CH:8]=2)[N:3]1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 11426996HCID 11426996, compound

Product 1

HCID 11439787HCID 11439787, compoundYield 26%

Procedure

At the temperature of 0C or less, 3.63 g of ethyl 2-[2,3-dioxo-7-(1H-imidazol-1-yl)-1,2,3,4-tetrahydroquinoxalin-1-yl]acetate was dissolved in 15 ml of fuming nitric acid under stirring. The resulting solution was heated to room temperature, stirred for one hour, and poured into ice water, followed by adjustment to about pH 2.0 with an aqueous solution of sodium hydroxide. The resulting insoluble matter was removed by filtration. To the filtrate, an aqueous solution of sodium hydroxide was added to adjust the pH of the resulting liquid to about pH 6.5. The resulting insoluble matter was collected by filtration, washed with water and dried under reduced pressure to give 1.07 g (26%, purity: about 95% (HPLC)) of ethyl 2-[2,3-dioxo-7-(1H-imidazol-1-yl)-6-nitro-1,2,3,4-tetrahydroquinoxalin-1-yl]acetate.

Workup

  1. stirringstirred for one hour
  2. customThe resulting insoluble matter was removed by filtration
  3. additionTo the filtrate, an aqueous solution of sodium hydroxide was added
  4. filtrationThe resulting insoluble matter was collected by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-3f23411cad254bfbaebd9b81fc999b37
Source dataset
uspto-grants-2000_08
Patent number
US06096743

Reaction notes

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