Stannous chloride dihydrate → HCID 21189995, compound

HRID 1781062Notes

Reaction equation

HRID 1781062 reaction equation
[Na+].[Cl:2][C:3]1[C:4]([F: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>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[F:17])[NH:14][C:11](=[O:12])[CH2:10][NH:9]2

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 21190019HCID 21190019, compound

Product 1

HCID 21189995HCID 21189995, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of N-(5'-chloro-4'-fluoro-2'-nitrophenyl)glycine sodium salt (0.650 g, 2.61 mmol) and tin (II) chloride dihydrate (1.770 g, 7.845 mmol) in ethanol (10.5 mL) was refluxed for 1 h. It was then cooled to room temperature and ~5 mL ethanol was removed under vacuum. The precipitated solid was collected by filtration under vacuum, washed with ethanol (3 mL) and dried to obtain 0.311 g (59%) title compound as an off-white powder; 1H NMR (DMSO-d6) δ3.69 (s, 2H), 6.08 (s, 1H), 6.65 (d, 1H, J=9.9 Hz), 6.71 (d, 1H, J=7.2 Hz), 10.39 (s, 1H). The solvent from the filtrate was removed under vacuum. The residue was diluted with water (15.0 mL) and the pH was adjusted with 10% Na2CO3 to ~9. The resulting suspension was extracted with ethyl acetate (50 mL). The ethyl acetate was dried over anhydrous Na2SO4 and removed under vacuum to yield further 0.118 g (22%) of pure (1H NMR) title compound for a combined yield of 81%.

Workup

  1. temperaturewas refluxed for 1 h
  2. custom~5 mL ethanol was removed under vacuum
  3. filtrationThe precipitated solid was collected by filtration under vacuum
  4. washwashed with ethanol (3 mL)
  5. customdried

Sources & evidence

ORD record
ord-453ac216b75e4661a8e649ffaaf4878f
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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