Ethyl 2-fluoro-5-nitrocarbanilate → Ethyl 5-amino-2-fluorocarbanilate

HRID 36798Notes

Reaction equation

HRID 36798 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:3]=1[NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8].[H][H]>[C].[Pd].C(O)C>[NH2:14][C:11]1[CH:12]=[CH:13][C:2]([F:1])=[C:3]([CH:10]=1)[NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 2754990Ethyl 2-fluoro-5-nitrocarbanilateHCID 178418361HCID 178418361, compound

Product 1

HCID 19937926Ethyl 5-amino-2-fluorocarbanilateYield 81%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

100.3 mg (10 wt %) of 5% palladium carbon (containing water) was added to a mixture of 1.00 g (4.39 mmol) of ethyl 2-fluoro-5-nitrocarbanilate and 20 ml of ethanol, and the resultant mixture was stirred until 309 ml of hydrogen was absorbed. The reaction mixture was filtered to remove the catalyst, and the solvent was then distilled off under a reduced pressure. Thus, 700 mg of the objective product (yield: 81%) was obtained in the form of light brown crystals.

Workup

  1. customwas absorbed
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. distillationthe solvent was then distilled off under a reduced pressure

Sources & evidence

ORD record
ord-b0f5a2a0fb2a496cacb3d62cd4530814
Source dataset
uspto-grants-1995_05
Patent number
US05416236

Reaction notes

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