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

HRID 1857402Notes

Reaction equation

HRID 1857402 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): δ 2.130 (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-2dcf9f10698e46c88a593fba81c2f152
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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