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

HRID 1857387Notes

Reaction equation

HRID 1857387 reaction equation
[Cl:1][C:2]1[C:3]([CH3:16])=[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>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[CH3:16])[NH:13][C:10](=[O:11])[CH2:9][NH:8]2

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 10014737HCID 10014737, compound

Product 1

HCID 100585236-Chloro-3,4-dihydro-7-methyl-2(1H)-quinoxalinoneYield 31.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(5'-chloro-4'-methyl-2'-nitrophenyl)glycine (1.000 g, 4.088 mmol, as prepared above) and tin (II) chloride dihydrate (2.767 g, 12.26 mmol, Aldrich, used as received) in ethanol (20.0 mL) was refluxed for 30 min. It was then cooled to room temperature and the precipitated solid was filtered, washed with ethanol (4.0 mL), and dried under vacuum to yield 0.251 g (31%) of the title compound as a yellow powder; 1H NMR (DMSO-d6): δ 2.093 (s, 3H), 3.657 (d, 2H, J=1.5 Hz), 5.984 (s, 1H), 6.583 (s, 1H), 6.632 (s, 1H), 10.253 (s, 1H).

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with ethanol (4.0 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-b6bb83e029094a43821ff57fab7d1ced
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

Loading…