Ethanol → HCID 21190002, compound

HRID 1068630Notes

Reaction equation

HRID 1068630 reaction equation
[Na+].[F:2][C:3]1[C:8](C)=[CH:7][C:6]([NH:10][CH2:11][C:12]([O-:14])=O)=[C:5]([N+:15]([O-])=O)[CH:4]=1.O.O.[Sn](Cl)Cl.[CH2:23](O)C>>[F:2][C:3]1[CH:4]=[C:5]2[C:6]([NH:10][CH2:11][C:12](=[O:14])[N:15]2[CH3:23])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 21189988HCID 21189988, compound

Product 1

HCID 21190002HCID 21190002, compound

Procedure

A mixture of N-(4-fluoro-5-methyl-2-nitrophenyl)glycine sodium salt(0. 125 g, 0.548 mmol) and tin (II) chloride dihydrate (0.370 g, 1.64 mmol, Aldrich, used as received) in ethanol (3.0 mL) was refluxed for 30 min. It was then cooled to room temperature and the solvent was removed under vacuum. The residue was diluted with water (4.0 mL) and basified with saturated NaHCO3 to pH ˜8. The resulting. suspension was extracted with ethyl acetate (30 mL). The extract was dried over Na2SO4 and evaporated to yield 0.032 g of the tide compound as a yellow powder, which was used for the next reaction; 1H NMR (DMSO-d6): 2.024 (s, 3H), 3.607 (s, 2H), 5.751 (s, 1H), 6.453 (d, 1H, J=9.9 Hz), 6.456 (d, 1H, J=8.1 Hz), 10.162 (s, 1H).

Workup

  1. temperaturewas refluxed for 30 min
  2. customthe solvent was removed under vacuum
  3. additionThe residue was diluted with water (4.0 mL)
  4. extractionsuspension was extracted with ethyl acetate (30 mL)
  5. dry with materialThe extract was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-58ace9f8845a49b38676970328c2d050
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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