HCID 58035641, compound → HCID 56828579, compound

HRID 1423338Notes

Reaction equation

HRID 1423338 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]>C(O)(=O)C.[Zn]>[NH2:14][C:11]1[CH:12]=[CH:13][C:2]([F:1])=[C:3]([CH:10]=1)[C:4]([O:6][CH:7]([CH3:8])[CH3:9])=[O:5]

Participants

4

Reactant 1

HCID 58035641HCID 58035641, compound

Product 1

HCID 56828579HCID 56828579, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Isopropyl 2-fluoro-5-nitrobenzoate (2.86 g, 12.6 mmol) was dissolved in glacial acetic acid (40 ml), and zinc dust (8.12 g, 126 mmol) was added as a solid with stirring under nitrogen. The mixture was stirred for 1 hour at room temperature, then the zinc filtered off and discarded. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (0 to 75% ethyl acetate in hexanes) to afford isopropyl 5-amino-2-fluorobenzoate. (2.48 g, 12.6 mmol). 100% yield. 199 (M+1).

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. filtrationthe zinc filtered off
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography (0 to 75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6765813c224d4acca3c8c0c493011dfa
Source dataset
uspto-grants-2015_01
Patent number
US08927582B2

Reaction notes

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