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

HRID 53814Notes

Reaction equation

HRID 53814 reaction equation
[Br:1][C:2]1[C:3]([Cl: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>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[Cl:16])[NH:13][C:10](=[O:11])[CH2:9][NH:8]2

Participants

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 10063959N-(5-Bromo-4-chloro-2-nitrophenyl)glycine

Product 1

HCID 100383166-bromo-7-chloro-3,4-dihydroquinoxalin-2(1H)-oneYield 18%

Procedure

A solution of N-(5-bromo-4-chloro-2-nitrophenyl)glycine (0.255 g, 0.824 mmol) and tin (II) chloride dihydrate (0.560 g, 2.48 Aldrich, used as received) was refluxed for 3 h. It was then cooled to r.t. and allowed to stand overnight at r.t. The white solid was filtered and dried to yield 0.038 g (18%) of pure title compound as white flakes; m.p. 230°-232° C.; 1H NMR (DMSO-d6): 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 to get a combined yield of 81%.

Workup

  1. filtrationThe white solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-efd0fa4734f647318d0ce9b841a75caa
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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