Sulfuric Acid → HCID 23193696, compound

HRID 48242Notes

Reaction equation

HRID 48242 reaction equation
[CH3:1][N:2]1[CH2:17][CH2:16][C:5]2[C:6]3[NH:7][C:8](=[O:15])[C:9](=[O:14])[NH:10][C:11]=3[CH:12]=[CH:13][C:4]=2[CH2:3]1.[N+:18]([O-])([O-:20])=[O:19].[K+].[OH-].[NH4+].[S:25](=[O:29])(=O)([OH:27])[OH:26]>>[CH3:1][S:25]([OH:27])(=[O:29])=[O:26].[CH3:1][N:2]1[CH2:17][CH2:16][C:5]2[C:6]3[NH:7][C:8](=[O:15])[C:9](=[O:14])[NH:10][C:11]=3[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[C:4]=2[CH2:3]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 104438838-Methyl-1,4,7,8,9,10-hexahydro-pyrido[4,3-f]quinoxaline-2,3-dione

Product 1

HCID 23193696HCID 23193696, compoundYield 35%

Procedure

A solution of the product from Example 22 (1.07 g,4.7 mmol) was dissolved in 20 ml sulfuric acid. Potassium nitrate (0.51 g, 5.0 mmol) was added in one portion, and the solution stirred for 1 hour. The solution was poured onto ice and made basic with ammonium hydroxide. The yellow solid which formed was filtered and washed with water and ether. The solid was purified by crystallization from water. The solid was suspended in water/DMF and 0.5 g methane sulphonic acid was added. The solution was concentrated, and the solid suspended in acetone, filtered and dried under vacuum (100° C.) to give the title compound (0.60 g, 35% yield), mp=292-294° C.

Workup

  1. additionThe solution was poured onto ice
  2. customThe yellow solid which formed
  3. filtrationwas filtered
  4. washwashed with water and ether
  5. customThe solid was purified by crystallization from water
  6. addition0.5 g methane sulphonic acid was added
  7. concentrationThe solution was concentrated
  8. filtrationfiltered
  9. customdried under vacuum (100° C.)

Sources & evidence

ORD record
ord-1cef07d946714503aee78dd53a48cb03
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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