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

HRID 1600729Notes

Reaction equation

HRID 1600729 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-275219ad44bd4a7780d28adfe9e2c26f
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

Loading…