Acetic Acid → 2-(4-Amino-3-fluorobenzamido)acetic acid

HRID 1399453Notes

Reaction equation

HRID 1399453 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[N+:20]([O-])=O)[C:5]([NH:7][CH2:8][C:9]([O:11]CC(Cl)(Cl)Cl)=[O:10])=[O:6].CC(O)=O>CCOC(C)=O.[Zn]>[NH2:20][C:19]1[CH:18]=[CH:17][C:4]([C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 867131242,2,2-Trichloroethyl 2-(3-fluoro-4-nitrobenzamido)acetate

Product 1

HCID 159257412-(4-Amino-3-fluorobenzamido)acetic acidYield 80.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
87.5 °C

Procedure

A mixture of 2,2,2-trichloroethyl 2-(3-fluoro-4-nitrobenzamido)acetate (40 mg, 0.1 mmol), zinc dust (105 mg, 1.61 mmol) and AcOH (3 mL) was stirred at 85-90° C. for 15 min. The reaction mixture was attained to rt and diluted with EtOAc (30 mL). The solution was filtered through super cell and washed with EtOAc (2×5 mL). The residue obtained after evaporation of the solvent was chromatographed using chloroform:methanol (60:40) as eluents to give the product as an off-white color solid (17 mg, 75%), mp 198-200° C.

Workup

  1. customwas attained to rt
  2. filtrationThe solution was filtered through super cell
  3. washwashed with EtOAc (2×5 mL)
  4. customThe residue obtained
  5. customafter evaporation of the solvent
  6. customwas chromatographed

Sources & evidence

ORD record
ord-7020cd48f6f041ae838d8217f80f6a5b
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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