Stannous chloride dihydrate → 167415-29-4

HRID 1781016Notes

Reaction equation

HRID 1781016 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 10060406167415-29-4Yield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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): δ3.684 (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

Sources & evidence

ORD record
ord-15e37d10d88148d9bb4bb35e4f153e2c
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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