Nitric Acid → Acea-1416

HRID 1600774Notes

Reaction equation

HRID 1600774 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[CH3:13].[N+:14]([O-])([OH:16])=[O:15].C(O)(C(F)(F)F)=[O:19]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:19])[C:8](=[O:12])[NH:9]2)=[C:4]([N+:14]([O-:16])=[O:15])[C:3]=1[CH3:13]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 100814077-Chloro-3,4-dihydro-6-methyl-2(1H)-quinoxalinone

Product 1

HCID 9816526Acea-1416

Procedure

To a stirred suspension of 7-chloro-3,4-Dihydro-6-methyl-quinoxaline-2(1H)-one (0.100 g, 0.51 mmol) in TFA (3.0 mL) prepared as in Example 8, excess fuming HNO3 (0.30 mL) was added and the resulting red solution was stirred overnight at room temperature. The solvent was removed under vacuum and the residue diluted with water (4.0 mL). The precipitated solid was filtered and dried under vacuum to yield 0.067 g (52%) pure (HPLC) title compound as a light yellow powder; mp-darkens at 340° C.; 1H NMR (DMSO-d6) δ 2.184 (s, 3H), 7.263 (s, 1H), 11.948 (s, 1H), 12.144 (s, 1H); Anal for C9H6ClN3O4.H2O calcd C, 40.85; H, 2.28; N, 15.87, found C, 40.63; H, 2.05; N, 15.75.

Workup

  1. additionwas added
  2. customThe solvent was removed under vacuum
  3. additionthe residue diluted with water (4.0 mL)
  4. filtrationThe precipitated solid was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f63ce01c30c24712a153f517b055b600
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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