Stannous chloride dihydrate → 167415-29-4

HRID 1857397Notes

Reaction equation

HRID 1857397 reaction equation
[Na+].[Br: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>[Br: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 15194586HCID 15194586, compound

Product 1

HCID 10060406167415-29-4

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(5'-bromo-4'-fluoro-2'-nitrophenyl)glycine sodium salt (0.450 g, 1.54 mmol, as prepared above) and tin (II) chloride dihydrate (1.039 g, 4.605 mmol, Aldrich, used as received) in ethanol (7.0 mL) was refluxed for 30 min. It was then cooled to room temperature and solvent was removed under vacuum. The residue was diluted with water (15.0 mL) and basified with 10% Na2CO3 to pH~8. The resulting suspension was extracted with ethyl acetate (100 mL). The ethyl acetate was dried over anhydrous Na2SO4 and removed under vacuum to yield 0.241 g (64%).of the title compound as a yellow powder, m.p. 214-216° C.; 1H NMR (DMSO-d6): δ 3.684 (s, 2H), 6.062 (s, 1H), 6.631 (d, 1H, J=9.3 Hz), 6.825 (d, 1H, J=6.6 Hz), 10.303 (s, 1H).

Workup

  1. customsolvent was removed under vacuum
  2. additionThe residue was diluted with water (15.0 mL)
  3. extractionThe resulting suspension was extracted with ethyl acetate (100 mL)
  4. dry with materialThe ethyl acetate was dried over anhydrous Na2SO4
  5. customremoved under vacuum
  6. customto yield 0.241 g (64%)

Sources & evidence

ORD record
ord-b5c83dead65749e0943377f8a0fb3107
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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