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

HRID 1781008Notes

Reaction equation

HRID 1781008 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): δ2.099 (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-cddbda38d6b149dc93731d7fe0f4c254
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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