Stannous chloride dihydrate → 5-Amino-7-chloro-6-methyl-1,4-dihydro-quinoxaline-2,3-dione

HRID 1600775Notes

Reaction equation

HRID 1600775 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[C:4]([N+:14]([O-])=O)[C:3]=1[CH3:17].O.O.[Sn](Cl)Cl>C(O)C>[NH2:14][C:4]1[C:3]([CH3:17])=[C:2]([Cl:1])[CH:11]=[C:10]2[C:5]=1[NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 9816526Acea-1416

Product 1

HCID 105611805-Amino-7-chloro-6-methyl-1,4-dihydro-quinoxaline-2,3-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 7-chloro-1,4-dihydro-6-methyl-5-nitroquinoxaline-2,3-dione (0.050 g, 0.20 mmol) and tin (II) chloride dihydrate (0.133 g, 0.60 mmol) in ethanol (1.0 mL) was refluxed for 6 h. The suspension was then cooled to room temperature and the solid was collected by vacuum filtration, washed with ethanol (1 mL), and dried further under vacuum to obtain 0.036 g (82%) pure (HPLC) title compound as an off-white solid; mp-darkens at 323° C.; 1H NMR (DMSO-d6) δ 2.09 (s, 3H), 5.47 (s, 2H), 6.46 (s, 1H), 11.15 (s, 1H), 11.72 (s, 1H).

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationthe solid was collected by vacuum filtration
  3. washwashed with ethanol (1 mL)
  4. customdried further under vacuum

Sources & evidence

ORD record
ord-9a9d95788131477ea03740450deafc42
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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