Ethyl 4-azido-2-fluoro-3-methylbenzoate → Ethyl 4-amino-2-fluoro-3-methylbenzoate

HRID 377274Notes

Reaction equation

HRID 377274 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:15])[C:5]=1[CH3:16])=[N+]=[N-]>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:15])[C:5]=1[CH3:16]

Participants

4

Reactant 1

HCID 19358340Ethyl 4-azido-2-fluoro-3-methylbenzoate

Product 1

HCID 19358316Ethyl 4-amino-2-fluoro-3-methylbenzoateYield 42.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 40 ml of ethanol was dissolved 2.00 g of ethyl 4-azido-2-fluoro-3-methylbenzoate, followed by adding thereto 0.40 g of 5% palladium-carbon, and the resulting mixture was stirred at room temperature for 5 hours under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a column chromatography (eluent; toluene:ethyl acetate=10:1) to obtain 0.75 g of ethyl 4-amino-2-fluoro-3-methylbenzoate as colorless crystals.

Workup

  1. additionby adding
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by a column chromatography (eluent; toluene:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-eadb04c04025484d943ddbacb40e5062
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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