Stannous chloride dihydrate → HCID 10037490, compound

HRID 53811Notes

Reaction equation

HRID 53811 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][CH2:10][C:11](O)=[O:12])=[C:4]([N+:14]([O-])=O)[CH:3]=1.BrC1C=C([N+]([O-])=O)C(F)=CC=1NCC(O)=O.O.O.[Sn](Cl)Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([NH:9][CH2:10][C:11](=[O:12])[NH:14]2)=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 100857532-[(4-Bromo-5-fluoro-2-nitrophenyl)amino]acetic AcidHCID 10469611N-(2-Bromo-5-fluoro-4-nitrophenyl)glycine

Product 1

HCID 10037490HCID 10037490, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of mixture of N-(4-bromo-5-fluoro-2-nitrophenyl)glycine and N-(2-bromo-5-fluoro-4-nitrophenyl)glycine (0.150 g, 0.512 mmol, as prepared above) and tin (II) chloride dihydrate (0.346 g, 1.53 mmol, Aldrich, used as received) in ethanol (3.0 mL) was refluxed for 30 min. It was then cooled to r.t. and the solvent was removed under vacuum. The residue was diluted with water (10 mL) and basified with saturated NaHCO3 (3.0 mL) to pH ~8. The resulting white suspension was extracted with ethyl acetate (30 mL). The extract was dried over Na2SO4 and evaporated to yield 0.050 g of crude product which was purified by precipitation from ethanol: water (1:1) to give 30 mg (24%) of pure title compound as a light yellow powder; m.p. 172° C. (decomposed); 1H NMR (DMSO-d6) 3.73 (s, 2H), 6.37 (s, 1H), 6.551 (d, 1H, J=10.2 Hz), 6.825 (d, 1H, J=6.6 Hz), 10.303 (s, 1H).

Workup

  1. temperaturewas refluxed for 30 min
  2. customthe solvent was removed under vacuum
  3. additionThe residue was diluted with water (10 mL)
  4. extractionThe resulting white suspension was extracted with ethyl acetate (30 mL)
  5. dry with materialThe extract was dried over Na2SO4
  6. customevaporated
  7. customto yield 0.050 g of crude product which
  8. customwas purified by precipitation from ethanol: water (1:1)

Sources & evidence

ORD record
ord-4a16f1d50b1b4fd79bc6bb228cb2e1e5
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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