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

HRID 1068604Notes

Reaction equation

HRID 1068604 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 (11) 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-fcef9e5cc29345dfb0c80d6518a8eff5
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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