Acetate → Methyl 5-amino-2-fluorobenzoate

HRID 1695549Notes

Reaction equation

HRID 1695549 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])(=O)C.O.O.[Sn](Cl)Cl>[OH-].[Na+]>[NH2:12][C:9]1[CH:10]=[CH:11][C:2]([F:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 175AcetateHCID 61436Stannous chloride dihydrateHCID 11217860Methyl 2-Fluoro-5-nitrobenzoate

Product 1

HCID 15621043Methyl 5-amino-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of methyl 2-fluoro-5-nitrobenzoate (1.96 g, 9.82 mmol) in ethyl is 5 acetate (40 ml) was added tin (II) chloride dihydrate (7.53 g, 33.38 mmol). The mixture was stirred overnight. Then aqueous NaOH solution (1 M, ca. 50 ml) was added to adjust the pH to 9. The layers were separated, the aqueous layer was extracted with ethyl acetate (4 times 20 ml) and the combined organic layers were washed with water and dried with Na2SO4. Filtration followed by evaporation of the solvent in vacuo afforded a yellowish solid, 1.48 g (90%) which was used in the next step without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (4 times 20 ml)
  3. washthe combined organic layers were washed with water
  4. dry with materialdried with Na2SO4
  5. filtrationFiltration
  6. customfollowed by evaporation of the solvent in vacuo
  7. customafforded a yellowish solid, 1.48 g (90%) which
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-704007bbe373484e9bb0c4c8dc84c131
Source dataset
uspto-grants-2012_04
Patent number
US08163724B2

Reaction notes

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