Water → 4-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)aniline

HRID 704090

Reaction equation

HRID 704090 reaction equation
O.[Cl:2][C:3]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:12])=[CH:7][C:6]([N+:19]([O-])=O)=[C:5]([F:22])[CH:4]=1>C(O)(=O)C.[Fe]>[Cl:2][C:3]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:12])=[CH:7][C:6]([NH2:19])=[C:5]([F:22])[CH:4]=1

Participants

5

Reactant 2

HCID 962WaterHCID 146178494-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)nitrobenzene

Product 1

HCID 146178504-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)anilineYield 75.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of iron powders (115 g), acetic acid (29 g) and water (551 g) was heated at 80° C., and a solution of the compound (III) (132 g) in acetic acid (200 g) was dropwise added thereto in 1 hour, followed by heating under reflux for 5 hours. The reaction mixture was filtered to remove insoluble materials, and the filtrate was extracted with ethyl acetate. The extract was concentrated under reduced pressure. The residue was distilled off under reduced pressure to give 4-chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)aniline (Compound (II)) (90 g). Yield, 75%. b.p., 145°-149° C./0.4 mmHg. m.p., 32°-34° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove insoluble materials
  5. extractionthe filtrate was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure
  7. distillationThe residue was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3586a230fbe5452ca004d53f026e5dff
Source dataset
uspto-grants-1991_01
Patent number
US04985570

Linked notes

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