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

HRID 1781005Notes

Reaction equation

HRID 1781005 reaction equation
[Cl:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([N+:13]([O-])=O)=[C:6]([NH:8][CH2:9][C:10](O)=[O:11])[CH:7]=1.O.O.[Sn](Cl)Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[CH3:16])[NH:13][C:10](=[O:11])[CH2:9][NH:8]2

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 10014737HCID 10014737, compound

Product 1

HCID 100585236-Chloro-3,4-dihydro-7-methyl-2(1H)-quinoxalinoneYield 31.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(5'-chloro-4'-methyl-2'-nitrophenyl)glycine (1.000 g, 4.088 mmol, as prepared above) and tin (II) chloride dihydrate (2.767 g, 12.26 mmol, Aldrich, used as received) in ethanol (20.0 mL) was refluxed for 30 min. It was then cooled to room temperature and the precipitated solid was filtered, washed with ethanol (4.0 mL), and dried under vacuum to yield 0.251 g (31%) of the title compound as a yellow powder; 1H NMR (DMSO-d6): δ2.093 (s, 3H), 3.657 (d, 2H, J=1.5 Hz), 5.984 (s, 1H), 6.583 (s, 1H), 6.632 (s, 1H), 10.253 (s, 1H).

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with ethanol (4.0 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-320d60f9a6d0463695a7580e7e302485
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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