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

HRID 1068601Notes

Reaction equation

HRID 1068601 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 ad 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 (DMSOd6): 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. filtrationwas filtered
  2. washwashed with ethanol (4.0 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-5d73c08ffd2b4730be7d25b437e83ff9
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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