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

HRID 1781021Notes

Reaction equation

HRID 1781021 reaction equation
[Na+].[Br: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>[Br: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 21189992HCID 21189992, compound

Product 1

HCID 117764637-Bromo-3,4-dihydro-6-methyl-2(1H)-quinoxalinoneYield 38.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4'-bromo-5'-methyl-2'-nitrophenyl)glycine sodium salt (0.200 g, 0.692 mmol, as prepared above) and tin (II) chloride dihydrate (0.468 g, 2.07 mmol, Aldrich, used as received) in ethanol (2.0 mL) was refluxed for 30 min. It was then cooled to room temperature. The precipitated solid was filtered and dried under vacuum to yield 0.064 g (38%) of the title compound as a yellow powder; 1NMR (DMSO-d6): δ2.130 (s, 3H), 3.674 (s, 2H), 6.120 (s, 1H), 6.583 (s, 1H), 6.868 (s, 1H), 10.284 (s, 1H).

Workup

  1. filtrationThe precipitated solid was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-170bfe4b83bd411a95c389639b5e87c3
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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