Stannous chloride dihydrate → 7-Chloro-3,4-dihydro-6-methyl-2(1H)-quinoxalinone

HRID 1857390Notes

Reaction equation

HRID 1857390 reaction equation
[Na+].[Cl:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([NH:10][CH2:11][C:12]([O-])=[O:13])=[C:5]([N+:15]([O-])=O)[CH:4]=1.O.O.[Sn](Cl)Cl>C(O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:6]([NH:10][CH2:11][C:12](=[O:13])[NH:15]2)=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 21189951HCID 21189951, compound

Product 1

HCID 100814077-Chloro-3,4-dihydro-6-methyl-2(1H)-quinoxalinoneYield 66.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4'-chloro-5'-methyl-2'-nitrophenyl)glycine sodium salt (0.300 g, 1.23 mmol, as prepared above) and tin (II) chloride dihydrate (0.830 g, 3.68 mmol, Aldrich, used as received) in ethanol (4.0 mL) was refluxed for 30 min. It was then cooled to room temperature and the precipitated solid was filtered, washed with ethanol (1.0 mL) and dried under vacuum to yield 0.160 g (66%) of the title compound as a yellow powder; 1H NMR (DMSO-d6): δ 2.099 (s, 3H), 3.655 (s, 2H), 6.037 (s, 1H), 6.538 (s, 1H), 6.685 (s, 1H), 10.241 (s, 1H).

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with ethanol (1.0 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-91883c4086964661bc478f15469268a5
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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