Hydrochloric Acid → HCID 22742091, compound

HRID 48170Notes

Reaction equation

HRID 48170 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[N+:13]([O-])=O.Cl.C(O)(C)C>[Fe].O>[NH2:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3776IsopropanolHCID 22742120Methyl 2-(4-fluoro-3-nitrophenyl)acetate

Product 1

HCID 22742091HCID 22742091, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Procedure

Iron powder (8.1 g) was added to a solution of methyl 4-fluoro-3-nitrophenylacetate (27.24 g, 0.128 mol) in a mixture of concentrated hydrochloric acid (1.5 ml), isopropanol (265 ml) and water (26.5 ml) and the mixture was stirred at room temperature for 1 hour. A second portion of iron powder (8.1 g) was added and the mixture was heated to reflux for 1 hour. A further quantity of concentrated hydrochloric acid was added and the mixture was refluxed for a further 1 hour. The mixture was cooled to room temperature, filtered through a plug of Hyflo® diatomaceous earth and the filtrate was evaporated in vacuo to give methyl 3-amino-4-fluorophenylacetate (22.98 g) which was used without further purification in the next step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturethe mixture was refluxed for a further 1 hour
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered through a plug of Hyflo® diatomaceous earth
  6. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c726521997da474c892a155de946a5aa
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

Loading…