Stannous chloride dihydrate → 6-bromo-7-chloro-3,4-dihydroquinoxalin-2(1H)-one

HRID 1068607Notes

Reaction equation

HRID 1068607 reaction equation
[Na+].[Br:2][C:3]1[C:4]([Cl:17])=[CH:5][C:6]([N+:14]([O-])=O)=[C:7]([NH:9][CH2:10][C:11]([O-])=[O:12])[CH:8]=1.O.O.[Sn](Cl)Cl>C(O)C>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[Cl:17])[NH:14][C:11](=[O:12])[CH2:10][NH:9]2

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 21189956HCID 21189956, compound

Product 1

HCID 100383166-bromo-7-chloro-3,4-dihydroquinoxalin-2(1H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(5′-bromo-4′-chloro-2′-nitrophenyl)glycine sodium salt (0.255 g, 0.824 mmol, as prepared above) and tin (II) chloride dihydrate (0.560 g, 2.48 mmol, Aldrich, used as received) in ethanol (6 mL) was refluxed for 3 h. It was then cooled to room temperature and allowed to stand overnight at room temperature. The white solid was filtered and dried to yield 0.038 g (18%) of the pure (1H NMR) title compound as white flakes; m.p. 230-232° C.; 1H NMR (DMSO-d6): δ 3.732 (s, 2H), 6.371 (s, 1H), 6.830 (s, 1H), 6.912 (s, 1H), 10.437 (s, 1H). Extraction of the filtrate with ethyl acetate (30 mL) gave 0.136 g (68%) more product for a combined yield of 86%. The product was used as such for the next reaction.

Workup

  1. filtrationThe white solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-695912f3f3534fa5ba7ff860b0187217
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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